1-Iodo-3,5-dimethylbenzene

clear light yellow liquid

General procedure: under oxygen, a sealed reaction tube was charged with KX (X = I, Br) (0.2 mmol), arylboronic acid (0.3 mmol), CuBrGeneral procedure: To a 15 mL test tube with septum Cs2CO3 (0.6 mmol, 195 mg), aromaticcarboxylic acid (1) (0.3 mmol), [Ir(dF(CF3)ppy)2dtbbpy]PF6 (D) (6 μmmol, 6.7 mg), Niodosuccinimide(NIS) (0.9 mmol, 202.5 mg) and I2 (15 μmol, 5 molpercent) were added. The tube was evacuated and backfilled with argon for three times, and then 3 mL of dry 1, 2-dichloroethane(DCE) was added through a syringer under argon. The tube was sealed with Parafilm M® andplaced in an oil bath with a contact thermometer, and the reaction was carried out at 50 °C underirradiation with 6 × 5 W blue LEDs (λmax = 455 nm). After 24 or 36 h, the resulting mixture wasfiltered through a 2 cm thick pad of silica, and the silica was washed with dichloromethane (DCM)(50 mL). The filtrate was collected and the solvent was removed in vacuo. The crude residue waspurified by silica gel flash column chromatography to provide the target product (2). (Note: Thereaction was very sensitive to moisture, and the yields sharply decreased to less than 5percent when0.01 equivalent of H2O was added to the reaction system).A Schlenk tube was charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (fine powder, dried, 300 mg, 2.00 mmol), evacuated and backfilled with argon. [TRANS-N, NAPOS;-DIMETHYL-1, ] 2-cyclohexanediamine (16 [ILL, ] 0.10 mmol, 10 [MOLpercent), ] 5-bromo-m- xylene [(136 GEL, ] 1.00 mmol), and solvent (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at [110 °C] for 23 h. The resulting suspension was allowed to reach room temperature. Ethyl acetate (2 mL) and dodecane (internal GC standard, 230 μL) were added to the reaction mixture. A 50 μL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are tabulated below.; A Schlenk tube was charged with CuI, sodium iodide (fine powder, dried, 300 mg, 2.00 mmol), evacuated and backfilled with argon. [N, NAPOS;-DIMETHYLETHYLENEDIAMINE, ] 5- [BROMO-M-XYLENE] (136 [UL, ] 1.00 mmol), and toluene (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at [110 °C] for 22 h. The resulting suspension was allowed to reach room temperature. Ethyl acetate (2 mL) and dodecane (internal GC standard, [230 GEL)] were added to the reaction mixture. A 50 pL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are tabulated below.Thirteen test tubes with screw threads were charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Meanwhile, a stock solution of 5-bromo-m-xylene (2.04 mL, 15.0 mmol) and dodecane (0.68 mL) in dioxane (15 mL) was prepared. To each test tube was added 1.18 mL of the stock solution and 0.10 mmol of ligand. The reaction mixtures in the sealed test tubes were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL) was added to each reaction mixture. A 50 iL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. See Figure 8.Nine Schlenk tubes were charged with Cul (9.6 mg, 0.050 mmol, 5.0 molpercent), ligand (if solid at room temperature; 0.10 mmol, 10 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Ligand (if liquid at room temperature, 0.10 mmol, 10 molpercent), [5-BROMO-M-XYLENE] (136 [IL, ] 1.00 mmol) and dioxane (1.0 mL) were added to each Schlenk tube. The reaction mixtures were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL), water (2 mL), and dodecane (230 [JL, ] internal GC standard) were added to each reaction mixture. A 50 [(IL] sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are compiled below, and represent averaged data from two runs.Nine Schlenk tubes were charged with Cul (9.6 mg, 0.050 mmol, 5.0 molpercent), ligand (if solid at room temperature; 0.10 mmol, 10 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Ligand (if liquid at room temperature, 0.10 mmol, 10 molpercent), [5-BROMO-M-XYLENE] (136 [IL, ] 1.00 mmol) and dioxane (1.0 mL) were added to each Schlenk tube. The reaction mixtures were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL), water (2 mL), and dodecane (230 [JL, ] internal GC standard) were added to each reaction mixture. A 50 [(IL] sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are compiled below, and represent averaged data from two runs.Thirteen test tubes with screw threads were charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Meanwhile, a stock solution of 5-bromo-m-xylene (2.04 mL, 15.0 mmol) and dodecane (0.68 mL) in dioxane (15 mL) was prepared. To each test tube was added 1.18 mL of the stock solution and 0.10 mmol of ligand. The reaction mixtures in the sealed test tubes were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL) was added to each reaction mixture. A 50 iL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. See Figure 8.Nine Schlenk tubes were charged with Cul (9.6 mg, 0.050 mmol, 5.0 molpercent), ligand (if solid at room temperature; 0.10 mmol, 10 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Ligand (if liquid at room temperature, 0.10 mmol, 10 molpercent), [5-BROMO-M-XYLENE] (136 [IL, ] 1.00 mmol) and dioxane (1.0 mL) were added to each Schlenk tube. The reaction mixtures were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL), water (2 mL), and dodecane (230 [JL, ] internal GC standard) were added to each reaction mixture. A 50 [(IL] sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are compiled below, and represent averaged data from two runs.Thirteen test tubes with screw threads were charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Meanwhile, a stock solution of 5-bromo-m-xylene (2.04 mL, 15.0 mmol) and dodecane (0.68 mL) in dioxane (15 mL) was prepared. To each test tube was added 1.18 mL of the stock solution and 0.10 mmol of ligand. The reaction mixtures in the sealed test tubes were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL) was added to each reaction mixture. A 50 iL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. See Figure 8.Nine Schlenk tubes were charged with Cul (9.6 mg, 0.050 mmol, 5.0 molpercent), ligand (if solid at room temperature; 0.10 mmol, 10 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Ligand (if liquid at room temperature, 0.10 mmol, 10 molpercent), [5-BROMO-M-XYLENE] (136 [IL, ] 1.00 mmol) and dioxane (1.0 mL) were added to each Schlenk tube. The reaction mixtures were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL), water (2 mL), and dodecane (230 [JL, ] internal GC standard) were added to each reaction mixture. A 50 [(IL] sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are compiled below, and represent averaged data from two runs.Nine Schlenk tubes were charged with Cul (9.6 mg, 0.050 mmol, 5.0 molpercent), ligand (if solid at room temperature; 0.10 mmol, 10 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Ligand (if liquid at room temperature, 0.10 mmol, 10 molpercent), [5-BROMO-M-XYLENE] (136 [IL, ] 1.00 mmol) and dioxane (1.0 mL) were added to each Schlenk tube. The reaction mixtures were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL), water (2 mL), and dodecane (230 [JL, ] internal GC standard) were added to each reaction mixture. A 50 [(IL] sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are compiled below, and represent averaged data from two runs.Nine Schlenk tubes were charged with Cul (9.6 mg, 0.050 mmol, 5.0 molpercent), ligand (if solid at room temperature; 0.10 mmol, 10 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Ligand (if liquid at room temperature, 0.10 mmol, 10 molpercent), [5-BROMO-M-XYLENE] (136 [IL, ] 1.00 mmol) and dioxane (1.0 mL) were added to each Schlenk tube. The reaction mixtures were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL), water (2 mL), and dodecane (230 [JL, ] internal GC standard) were added to each reaction mixture. A 50 [(IL] sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are compiled below, and represent averaged data from two runs.Thirteen test tubes with screw threads were charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Meanwhile, a stock solution of 5-bromo-m-xylene (2.04 mL, 15.0 mmol) and dodecane (0.68 mL) in dioxane (15 mL) was prepared. To each test tube was added 1.18 mL of the stock solution and 0.10 mmol of ligand. The reaction mixtures in the sealed test tubes were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL) was added to each reaction mixture. A 50 iL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. See Figure 8.Nine Schlenk tubes were charged with Cul (9.6 mg, 0.050 mmol, 5.0 molpercent), ligand (if solid at room temperature; 0.10 mmol, 10 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Ligand (if liquid at room temperature, 0.10 mmol, 10 molpercent), [5-BROMO-M-XYLENE] (136 [IL, ] 1.00 mmol) and dioxane (1.0 mL) were added to each Schlenk tube. The reaction mixtures were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL), water (2 mL), and dodecane (230 [JL, ] internal GC standard) were added to each reaction mixture. A 50 [(IL] sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are compiled below, and represent averaged data from two runs.Thirteen test tubes with screw threads were charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Meanwhile, a stock solution of 5-bromo-m-xylene (2.04 mL, 15.0 mmol) and dodecane (0.68 mL) in dioxane (15 mL) was prepared. To each test tube was added 1.18 mL of the stock solution and 0.10 mmol of ligand. The reaction mixtures in the sealed test tubes were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL) was added to each reaction mixture. A 50 iL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. See Figure 8.Thirteen test tubes with screw threads were charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Meanwhile, a stock solution of 5-bromo-m-xylene (2.04 mL, 15.0 mmol) and dodecane (0.68 mL) in dioxane (15 mL) was prepared. To each test tube was added 1.18 mL of the stock solution and 0.10 mmol of ligand. The reaction mixtures in the sealed test tubes were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL) was added to each reaction mixture. A 50 iL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. See Figure 8.Thirteen test tubes with screw threads were charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Meanwhile, a stock solution of 5-bromo-m-xylene (2.04 mL, 15.0 mmol) and dodecane (0.68 mL) in dioxane (15 mL) was prepared. To each test tube was added 1.18 mL of the stock solution and 0.10 mmol of ligand. The reaction mixtures in the sealed test tubes were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL) was added to each reaction mixture. A 50 iL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. See Figure 8.Thirteen test tubes with screw threads were charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Meanwhile, a stock solution of 5-bromo-m-xylene (2.04 mL, 15.0 mmol) and dodecane (0.68 mL) in dioxane (15 mL) was prepared. To each test tube was added 1.18 mL of the stock solution and 0.10 mmol of ligand. The reaction mixtures in the sealed test tubes were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL) was added to each reaction mixture. A 50 iL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. See Figure 8.Thirteen test tubes with screw threads were charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Meanwhile, a stock solution of 5-bromo-m-xylene (2.04 mL, 15.0 mmol) and dodecane (0.68 mL) in dioxane (15 mL) was prepared. To each test tube was added 1.18 mL of the stock solution and 0.10 mmol of ligand. The reaction mixtures in the sealed test tubes were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL) was added to each reaction mixture. A 50 iL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. See Figure 8.Thirteen test tubes with screw threads were charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Meanwhile, a stock solution of 5-bromo-m-xylene (2.04 mL, 15.0 mmol) and dodecane (0.68 mL) in dioxane (15 mL) was prepared. To each test tube was added 1.18 mL of the stock solution and 0.10 mmol of ligand. The reaction mixtures in the sealed test tubes were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL) was added to each reaction mixture. A 50 iL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. See Figure 8.Nine Schlenk tubes were charged with Cul (9.6 mg, 0.050 mmol, 5.0 molpercent), ligand (if solid at room temperature; 0.10 mmol, 10 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Ligand (if liquid at room temperature, 0.10 mmol, 10 molpercent), [5-BROMO-M-XYLENE] (136 [IL, ] 1.00 mmol) and dioxane (1.0 mL) were added to each Schlenk tube. The reaction mixtures were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL), water (2 mL), and dodecane (230 [JL, ] internal GC standard) were added to each reaction mixture. A 50 [(IL] sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are compiled below, and represent averaged data from two runs.Nine Schlenk tubes were charged with Cul (9.6 mg, 0.050 mmol, 5.0 molpercent), ligand (if solid at room temperature; 0.10 mmol, 10 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Ligand (if liquid at room temperature, 0.10 mmol, 10 molpercent), [5-BROMO-M-XYLENE] (136 [IL, ] 1.00 mmol) and dioxane (1.0 mL) were added to each Schlenk tube. The reaction mixtures were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL), water (2 mL), and dodecane (230 [JL, ] internal GC standard) were added to each reaction mixture. A 50 [(IL] sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are compiled below, and represent averaged data from two runs.A Schlenk tube was charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (fine powder, dried, 300 mg, 2.00 mmol), evacuated and backfilled with argon. [TRANS-N, NAPOS;-DIMETHYL-1, ] 2-cyclohexanediamine (16 [ILL, ] 0.10 mmol, 10 [MOLpercent), ] 5-bromo-m- xylene [(136 GEL, ] 1.00 mmol), and solvent (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at [110 °C] for 23 h. The resulting suspension was allowed to reach room temperature. Ethyl acetate (2 mL) and dodecane (internal GC standard, 230 μL) were added to the reaction mixture. A 50 μL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are tabulated below.A Schlenk tube was charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (fine powder, dried, 300 mg, 2.00 mmol), evacuated and backfilled with argon. [TRANS-N, NAPOS;-DIMETHYL-1, ] 2-cyclohexanediamine (16 [ILL, ] 0.10 mmol, 10 [MOLpercent), ] 5-bromo-m- xylene [(136 GEL, ] 1.00 mmol), and solvent (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at [110 °C] for 23 h. The resulting suspension was allowed to reach room temperature. Ethyl acetate (2 mL) and dodecane (internal GC standard, 230 μL) were added to the reaction mixture. A 50 μL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are tabulated below.A Schlenk tube was charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (fine powder, dried, 300 mg, 2.00 mmol), evacuated and backfilled with argon. [TRANS-N, NAPOS;-DIMETHYL-1, ] 2-cyclohexanediamine (16 [ILL, ] 0.10 mmol, 10 [MOLpercent), ] 5-bromo-m- xylene [(136 GEL, ] 1.00 mmol), and solvent (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at [110 °C] for 23 h. The resulting suspension was allowed to reach room temperature. Ethyl acetate (2 mL) and dodecane (internal GC standard, 230 μL) were added to the reaction mixture. A 50 μL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are tabulated below.A Schlenk tube was charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (fine powder, dried, 300 mg, 2.00 mmol), evacuated and backfilled with argon. [TRANS-N, NAPOS;-DIMETHYL-1, ] 2-cyclohexanediamine (16 [ILL, ] 0.10 mmol, 10 [MOLpercent), ] 5-bromo-m- xylene [(136 GEL, ] 1.00 mmol), and solvent (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at [110 °C] for 23 h. The resulting suspension was allowed to reach room temperature. Ethyl acetate (2 mL) and dodecane (internal GC standard, 230 μL) were added to the reaction mixture. A 50 μL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are tabulated below.A Schlenk tube was charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (fine powder, dried, 300 mg, 2.00 mmol), evacuated and backfilled with argon. [TRANS-N, NAPOS;-DIMETHYL-1, ] 2-cyclohexanediamine (16 [ILL, ] 0.10 mmol, 10 [MOLpercent), ] 5-bromo-m- xylene [(136 GEL, ] 1.00 mmol), and solvent (1.0 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at [110 °C] for 23 h. The resulting suspension was allowed to reach room temperature. Ethyl acetate (2 mL) and dodecane (internal GC standard, 230 μL) were added to the reaction mixture. A 50 μL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. The results are tabulated below.Thirteen test tubes with screw threads were charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Meanwhile, a stock solution of 5-bromo-m-xylene (2.04 mL, 15.0 mmol) and dodecane (0.68 mL) in dioxane (15 mL) was prepared. To each test tube was added 1.18 mL of the stock solution and 0.10 mmol of ligand. The reaction mixtures in the sealed test tubes were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL) was added to each reaction mixture. A 50 iL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. See Figure 8.Thirteen test tubes with screw threads were charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Meanwhile, a stock solution of 5-bromo-m-xylene (2.04 mL, 15.0 mmol) and dodecane (0.68 mL) in dioxane (15 mL) was prepared. To each test tube was added 1.18 mL of the stock solution and 0.10 mmol of ligand. The reaction mixtures in the sealed test tubes were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL) was added to each reaction mixture. A 50 iL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. See Figure 8.Thirteen test tubes with screw threads were charged with Cul (9.6 mg, 0.0504 mmol, 5.0 molpercent), sodium iodide (300 mg, 2.00 mmol), evacuated and backfilled with argon. Meanwhile, a stock solution of 5-bromo-m-xylene (2.04 mL, 15.0 mmol) and dodecane (0.68 mL) in dioxane (15 mL) was prepared. To each test tube was added 1.18 mL of the stock solution and 0.10 mmol of ligand. The reaction mixtures in the sealed test tubes were stirred at [110 °C] for 22 h. The resulting suspensions were allowed to reach room temperature. Ethyl acetate (2 mL) was added to each reaction mixture. A 50 iL sample of the supernatant solution was diluted with ethyl acetate (1 mL) and analyzed by GC. See Figure 8.

suzuki reaction

Molecular Weight:232.06
XLogP3:3.7
Exact Mass:231.97490
Monoisotopic Mass:231.97490
Heavy Atom Count:9
Complexity:80.6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes