90868-92-1

623-00-7

23719-80-4

90868-92-1

A solution of 4-bromobenzonitrile (6.30 g) in tetrahydrofuran (50 mL) was added dropwise to an ice-bath-cooled 0.5 M cyclopropylmagnesium bromide tetrahydrofuran solution (200 mL) over 20 minutes. The reaction mixture was stirred continuously for 5.5 hours under ice bath conditions. Subsequently, methanol (100 mL) was added slowly over 20 minutes to quench the reaction. After batchwise addition of sodium borohydride (2.65 g), the reaction mixture was gradually warmed to room temperature and stirred overnight. Upon completion of the reaction, saturated aqueous NaHCO3 was added and the pH of the mixture was adjusted to 8-9 with 1 M hydrochloric acid.The reaction mixture was extracted with dichloromethane and the organic phases were combined, washed with water and dried over anhydrous magnesium sulfate. The organic phase was concentrated under reduced pressure to give the crude product as an oil. The oil was redissolved in dichloromethane and extracted with 1 M hydrochloric acid. The combined aqueous phases were alkalized to pH 8-9 with 4M NaOH aqueous solution and extracted again with dichloromethane. The combined organic phases were washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give α-cyclopropyl-4-bromobenzylamine as an oily product. Yield: 5.56 g (72% yield); mass spectrum (ESI+): m/z = 209/211 (Br)[M+H-NH3]+.