Ammonium Chloride → 4-Bromo-3-methoxyaniline

Participants

Reaction Steps

2-Bromo-5-nitroanisole (31 g, 134 mmoles) in methanol (700 ml) was added to a mixture of iron powder (22.5 g, 400 mmoles), and ammonium chloride (33.5 g, 630 mmoles) in water (600 ml). The mixture was heated under reflux for 3 hrs. The mixture was allowed to cool and filtered. The filtrate was concentrated in vacuo and the residue partitioned between water and dichloromethane. The organic phase was dried (Na2SO4), filtered and evaporated to dryness to give the title compound (D1) (25 g, 93%).

Provenance & Evidence