549488-77-9

544-92-3

175278-17-8

549488-77-9

To a solution of 2-bromo-4-(trifluoromethoxy)aniline (15.1 g, 60.0 mmol) in N-methylpyrrolidone (100 mL) was added cuprous cyanide (10.6 g, 118 mmol), and the reaction mixture was stirred at 0 °C for 6.5 hours. Upon completion of the reaction, the mixture was cooled to room temperature and poured into a mixture of ice water (300 mL) and ammonia (350 mL). The resulting brown precipitate was collected by filtration, washed with water (150 mL), and then the precipitate was dissolved in dichloromethane (350 mL). Insoluble material was removed by filtration and the filtrate was washed with brine (100 mL) and dried over anhydrous sodium sulfate. Purification by silica gel column chromatography (eluent:heptane/ethyl acetate=95:5 to 25:75) afforded 2-amino-5-trifluoromethoxybenzonitrile (9.09 g, 76% yield) as a brown solid. Mass spectrum (MS): m/e = 405.1 [2M + H]+.