Hydrochloric Acid → 1-(3-Bromophenyl)ethanamine

Participants

Reaction Steps

A mixture of 3′-bromoacetophenone (2.66 mL, 20 mmol), ammonium formate (6.31 g, 100 mmol) and dichloro(pentamethylcyclopentadienyl)rhodium(III)dimer (124 mg, 0.2 mmol) in anhydrous methanol (20 mL) under an atmosphere of nitrogen was heated at reflux for 5 hours then allowed to cool to room temperature overnight. The mixture was diluted with water (20 mL), acidified to pH 2 with dilute aqueous hydrochloric acid (2M) and washed with dichloromethane (2×60 mL). The aqueous solution was basified to pH 12 with solid potassium hydroxide, extracted with dichloromethane (3×50 mL) and the extracts washed with brine (50 mL), dried (Na2SO4) and concentrated under reduced pressure to give 1-(3-bromophenyl)ethanamine (3.4 mg, 85%) as a yellow liquid.

Provenance & Evidence