Acetic Acid → N-Benzyl-3-bromoaniline

Participants

Reaction Steps

A solution of 3-bromo aniline (5 g, 29 mmol), benzaldehyde (3.24 ml, 32 mmol) and acetic acid (2.49 ml, 44 mmol) in dry tetrahydrofuran (50 ml) was stirred at room temperature for 3 hrs. Sodium borohydride (2.755 g, 73 mmol) was added and the reaction stirred at room temperature overnight. The reaction mixture was quenched with water (100 ml) and extracted with dichloromethane (3×100 ml). The organic extracts were combined, dried (magnesium sulphate) and concentrated in vacuo. HPLC retention time 7.7 min. Mass spectrum (ES+) m/z 263 (M+H)

Provenance & Evidence