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

Participants

Reaction Steps

A mixture 2-bromo-4-nitroanisole (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 stirred at reflux for 2 hours. The mixture was allowed to cool to ambient temperature and filtered through a pad of Hyflo™ (washed with 25% acetic acid/water). The filtrate was extracted with ethyl acetate (2×250 ml) and the organic layer was dried over sodium sulphate. Removal of the solvent in vacuo left an oil which was chromatographed on silica eluting with 40% ethyl acetate/hexane to give the title compound as a brown solid (10.32 g, 79%); m/z (ES+) 202 ([M+H]+).

Provenance & Evidence