Dimethylformamide → Methyl 2-chloro-4-cyanobenzoate

Participants

Reaction Steps

A mixture of triphenylphosphine polymer bound (239 mg, 0.72 mmol) and palladium(II) acetate (75 mg, 0.33 mmol) was prepared in DMF (12 mL) under nitrogen atmosphere and stirred at RT for 2 hours. Zinc cyanide (561 mg, 4.77 mmol) and methyl 4-bromo-2-chlorobenzoate (1.19 g, 4.77 mmol) were added and the resulting mixture was heated under microwave irradiation at 140° C. for 50 minutes. The reaction mixture was filtered and the resin was washed with Et2O (3×10 mL). The combined organic layers were washed with water (3×5 mL) and brine (10 mL), dried (MgSO4) and concentrated under vacuum to give the title compound as a white powder. 1H NMR (DMSO-d6, 300 MHz) δ 8.23 (m, 1H), 7.96 (m, 2H), 3.90 (s, 3H). HPLC (Method A) Rt 3.39 min (Purity: 97.6%).

Provenance & Evidence