ethyl2-(4-cyanophenyl)acetate

General procedure: after standard cycles of evacuation and back-filling with dry and pure nitrogen, an oven-dried Schlenk tube equipped with a magnetic stirring bar was charged with Pd source (see Table 1, Table 2, Table 3 and Table 4), ligand (see Table 1, Table 2, Table 3 and Table 4), N, N-dimethylpyridin-4-amine (DMAP, see Table 1, Table 2, Table 3 and Table 4), and ethyl potassium malonate (see Table 1, Table 2, Table 3 and Table 4). The tube was evacuated and backfilled with argon (this procedure was repeated three times). Under a counter flow of argon, aryl halide (see Table 1, Table 2, Table 3 and Table 4) and solvent (see Table 1, Table 2, Table 3 and Table 4) were added by syringe. The tube was sealed and stirred at room temperature for 10 min. Then the tube was connected to the Schlenk line, which was full of argon, stirred in a preheated oil bath (140-150 °C) for the appointed time (20-25 h). Upon completion of the reaction, the mixture was cooled to room temperature and diluted with diethyl ether, and the yields were determined by gas chromatography using 1, 3-dimethoxybenzene as the internal standard.Preparation 56 ethyl 2-(4-cyanophenyl)acetate [0247] Combined ethyl 2-(4-bromophenyl)acetate (30 g, 0.123 mol) and MP (200 mL). Then CuCN (33 g, 0.370 mol) was added in portions and then degassed and refilled with nitrogen three times. Then Cul (4.7 g, 0.0247mol) was added in one portion. The reaction was degassed and refilled with nitrogen three times and then heated to 160°C for 4 hours. Then the reaction was heated to 180°C for another 3 hours. The solution was then cooled to room temperature and diluted with EtOAc (500 mL) and water (500 mL). After stirring for 10 mins, the reaction was filtered and the aqueous layer was extracted with EtOAc (500 mLx2). The combined organic layers were washed with brine, dried over NaGeneral procedure: after standard cycles of evacuation and back-filling with dry and pure nitrogen, an oven-dried Schlenk tube equipped with a magnetic stirring bar was charged with Pd source (see Table 1, Table 2, Table 3 and Table 4), ligand (see Table 1, Table 2, Table 3 and Table 4), N, N-dimethylpyridin-4-amine (DMAP, see Table 1, Table 2, Table 3 and Table 4), and ethyl potassium malonate (see Table 1, Table 2, Table 3 and Table 4). The tube was evacuated and backfilled with argon (this procedure was repeated three times). Under a counter flow of argon, aryl halide (see Table 1, Table 2, Table 3 and Table 4) and solvent (see Table 1, Table 2, Table 3 and Table 4) were added by syringe. The tube was sealed and stirred at room temperature for 10 min. Then the tube was connected to the Schlenk line, which was full of argon, stirred in a preheated oil bath (140-150 °C) for the appointed time (20-25 h). Upon completion of the reaction, the mixture was cooled to room temperature and diluted with diethyl ether, and the yields were determined by gas chromatography using 1, 3-dimethoxybenzene as the internal standard.Step 0 (Intermediate A): see example 85.[0556]Step 1: To a stirred solution of 2-(4-bromophenyl)acetic acid (2 g, 9.3 mmol) in ethanol (10 mL) were added sulfuric acid (0.3 mL). The reaction mixture was refluxed for overnight and cooled to room temperature. The solvent was evaporated. The residue was dissolved with ethylacetate and neutralized with NaHCOStep 2: To a solution of ethyl 2-(4-bromophenyl)acetate (3.24 g, 13.32 mmol) in anhydrous dimethylformamide was added zinc cyanide (939 mg, 7.99 mmol), tetrakis(triphenylphosphine)palladium(0) (770 mg, 0.67 mmol). Step 2: To a stirred solution of ethyl 2-(4-bromophenyl)acetate (2.1 g, 8.445 mmol) in anhydrous dimethylformamide were added zinc cyanide (1 .5 g, 12.668 mmol) and tetrakis(triphenylphosphine) palladium (1 .0 g, 0.845 mmol). The reaction mixture was refluxed for overnight then cooled to room temperature. The mixture was filtered using celite pad and the filtrate was evaporated. The residue was diluted with ethylacteate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filterate was concentrated under reduced pressure to get the crude. The crude was purified by column chromatography. Ethyl 2-(4-cyanophenyl)acetate (0.8 g) was obtained as 49 percent yield.Preparation 26

Molecular Weight:189.21
XLogP3:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:189.078978594
Monoisotopic Mass:189.078978594
Topological Polar Surface Area:50.1
Heavy Atom Count:14
Complexity:233
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes