2-Bromo-4-nitroanisole → 3-Bromo-4-methoxyaniline

Participants

Reaction Steps

A mixture 3-bromo-4-methoxynitrobenzene (15 g, 64.6 mmol) and iron powder (27.3 g, 0.49 mol) in water (100 ml) and glacial acetic acid (25 ml) was heated under reflux for 2 h. The mixture was cooled and filtered through a pad of Hyflo™, washing with 25% acetic acid/water. The filtrate was extracted with ethyl acetate (2×250 ml) and the combined organic fractions were dried (Na2SO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica eluting with hexane/EtOAc (60:40) to give the title compound as a brown solid (10.32 g, 79%). m/z (ES+) 202 (M+1).

Provenance & Evidence