A solution of 3-bromo-2-methylbenzamide (500 mg, 2.340 mmol) and pyridine (0.60 mL, 7.42 mmol) in dichloromethane (10 mL) was cooled to 0 °C and then trifluoroacetic anhydride (1.0 mL, 7.08 mmol) was slowly added. The reaction mixture was gradually warmed to room temperature and stirred continuously for 15 hours. Upon completion of the reaction, the mixture was partitioned between ethyl acetate (100 mL) and 1M HCl solution (25 mL). The organic phase was washed sequentially with saturated NaHCO3 solution (25 mL) and brine (25 mL), dried over Na2SO4, filtered and concentrated to give 423 mg (92%) of 3-bromo-2-methylbenzonitrile as a light yellow oil, which could be used for the next reaction without further purification.
