1-Chloro-3-iodobenzene

  Description  

1-Chloro-3-iodobenzene

625-99-0

C6H4ClI

  Basic Info  

1-Chloro-3-iodobenzene

Benzene,1-chloro-3-iodo-;1-Chloro-3-iodobenzene;m-Chloroiodobenzene;3-Chloro-1-iodobenzene;3-Chloroiodobenzene;3-Iodochlorobenzene;m-Chlorophenyl iodide;3-Chlorophenyl iodide;m-Chloroiodobenzene;1-Iodo-3-chlorobenzene;NSC 32861

  Characteristics  

  Safety Information  

Use and Manufacturing  

General procedure: A mixture of the arylboronic acid (0.55mmol), KF (96mg, 1.65mmol) and IGeneral procedure: Arylboronic acid 1 (0.5 mmol) and K2CO3 (1 mmol, 138.0mg) were added to a 20 mL Schlenk-tube equipped with amagnetic stir bar. The tube was evacuated twice and backfilledwith N2. MeCN (2 mL) and I2 (0.75 mmol, 191 mg)were added to the tube at r.t. under a stream of N2, and thetube was sealed and placed into a pre-heated oil bath at 80 °Cfor 8–12 h. The resulting solution was cooled to r.t. and H2O(10 mL) was added. The aq layer was extracted with EtOAc (3 × 5 mL). For products 2s and 2t, HCl (1 M) was added tothe aq solution until pH 2 before extraction. The combinedorganic phase was dried over anhydrous Na2SO4, filteredand concentrated by rotary evaporation. Purification of theresidue by column chromatography on silica gel providedthe desired product 2a–vGeneral procedure: To a suspension of aryl diazofluoroborate (1 mmol) inwater (3mL), aqueous solution of potassium iodide (1.5 mmol in 2mL H2O) was added in single lot at room temperature.Reaction mixture was stirred for specific time (Table 2).The solid product was separated by filtration and the liquidproducts were separated by extraction in diethyl ether (5mL).The organic layer was dried over anhydrous Na2SO4 andsolvent was removed at room temperature afforded pure iodocompounds in excellent yields. Further all synthesized compoundswere characterized and confirmed by comparisonwith reported aryl iodides.General 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), NIS (1.5mmol, 337.5 mg) and I2 (60 μmol, 20 molpercent) were added. The tube was evacuated and backfilledwith argon for three times, and then 3 mL of dry DCE was added through a syringer under argon.The tube was sealed with Parafilm Mr® and placed in an oil bath with a contact thermometer, andthe reaction was carried out at 50 °C under irradiation with 6 × 5 W blue LEDs (λmax = 455 nm).After 24 h or 36 h, the resulting mixture was filtered through a 2 cm thick pad of silica, and thesilica was washed with DCM) (50 mL). The filtrate was collected and the solvent was removed invacuo. The crude residue was purified by silica gel flash column chromatography to provide thetarget product (2). (Note: The reaction was very sensitive to moisture, and the yields sharplydecreased to less than 5percent when 0.01 equivalent of H2O was added to the reaction system).

suzuki reaction