Formic Acid → 1-(3-Bromophenyl)ethanamine

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromoacetophenone (10.0 g, 50 mmol), formic acid (12.0 g, 250 mmol) and formamide (50 mL) was heated at 165-180° C. with stirring for 24 h. The reaction mixture was cooled to room temperature and extracted with toluene; the extract was concentrated in vacuo. The residue was mixed with 3N hydrochloric acid (20 mL) and heated at reflux for 48 h, cooled to room temperature, washed with ether and neutralized with 20% aqueous NaOH solution. The neutralized solution was extracted with ether; the extract was dried over solid KOH and concentrated in vacuo to provide the title compounds as a light brown oil (5.7 g, 57%). 1H NMR (400 MHz, CDCl3): δ 7.53 (s, 1H), 7.37 (d, 1H), 7.29 (d, 1H), 7.21 (t, 1H), 4.14 (br d, 3H), 1.39 (d, 3H). MS (ESI) m/z: Calculated: 199; Observed: 200 (M+H+).

Provenance & Evidence