Hydrochloric Acid → (4-Bromo-2-chlorophenyl)methanamine

Participants

Reaction Steps

To a solution of 4-bromo-2-chlorobenzonitrile (2 g, 9.24 mmol) in Tetrahydrofuran (THF) (10 ml) was added aluminum hydride (37.0 ml, 18.48 mmol) in THF. The reaction mixture was acidified with 1N HCl to pH=4. The mixture was washed with ether (2×50 ml). The aqueous layer was separated and it was adjusted with 1N NaOH to pH=10. The mixture was extracted with ether. The organic layer was separated and dried over Na2SO4. The solvent was evacuated to give 1-(4-bromo-2-chlorophenyl)methanamine (1.8 g, 8.2 mmol, 88%). MS (ES+): m/e 220, 222 [M+H]+.

Provenance & Evidence