Synthesis
The general procedure for the synthesis of (4-bromo-2-methylphenyl)methanamine hydrochloride from 4-bromo-2-methylbenzonitrile was as follows: to a solution of 4-bromo-2-methylbenzenecarbonitrile (3 g, 15 mmol) in tetrahydrofuran (THF, 20 mL) was slowly added borane-tetrahydrofuran complex (BH3-THF, 45 mL, 45 mmol). The reaction mixture was stirred at 0 °C for 1 h. The temperature was gradually increased to 80 °C and the reaction was maintained for 16 hours. After completion of the reaction, the reaction was quenched with methanol (MeOH). After concentration under reduced pressure to remove the solvent, the residue was treated with saturated hydrogen chloride/ethyl acetate (HCl/EtOAc) solution with stirring and subsequently filtered. The resulting solid was washed with ether (20 mL x 3) and finally dried under vacuum to afford the target product (4-bromo-2-methylphenyl)methylamine hydrochloride (3.2 g, yield: 90%) as a white solid. Electrospray ionization mass spectrometry (ESI-MS) showed molecular ion peak (M + H)+: 200.1.
