Hydrochloric Acid → 3-(Bromomethyl)aniline

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of 1-(bromomethyl)-3-nitrobenzene (40 g; 0.18 mol) and iron powder (31 g; 0.55 mol) in EtOH (1000 mL) was added concentrated HCl (33.8 g, 0.93 mol) at r.t. The mixture was stirred at 85° C. for 2 hrs, cooling to r.t. and filtered. The filtrate was evaporated and the residue was solved in EtOAc and washed with brine, dried (Na2SO4) and concentrated to give the 3-(bromomethyl)aniline (30 g, 87% yield) as a yellow solid. 1H NMR: (400 MHz, MeOD) δ 7.59-7.56 (m, 1H), 7.54 (t, 1H), 7.39 (d, 1H), 7.38-7.34 (m, 1H), 4.73 (s, 2H).

Provenance & Evidence