Hydrochloric Acid → 5-Bromo-2-methoxyaniline

Participants

Reaction Steps

Iron powder (16.1 g) was added to a stirring mixture of 4-bromo-2-nitroanisole (13.92 g, 60 mmol) in 200 ml ethanol. The reaction mixture was heated to reflux, whereupon 50 ml of 0.5N HCl solution was added dropwise over a 45 minute period. The reaction mixture was then refluxed for an additional 3 hours then was allowed to cool to room temperature and was then filtered through celite and the resulting filtrate was concentrated under vacuum. The resulting solid was suspended in saturated NaHCO3 solution, then collected by filtration, and washed with water. The solid was recrystallized from cyclohexane to yield 4-bromo-2-aminoanisole (9.90 g, 82%). m.p. 93° C.; 1H NMR (300 MHz, CDCl3) δ6.69 (2H, m), 6.52 (1H, d, J=9.0 Hz), 3.72 (3H, s).

Provenance & Evidence