Sodium Dithionite → 2-Amino-6-bromophenol

Participants

Reaction Steps

2-Bromo-6-nitrophenol (1.506 g, 0.0057 mol, containing 2,4-di-bromo-6-nitrophenol, 18% w/w) and sodium hydrosulfite (3.05 g, 85%, 0.015 mol) were heated at reflux in ethanol/water (50 ml of a 5:1 v/v mixture). After 2 hours, the reaction mixture was diluted with water (150 ml) and extracted with dichloromethane (3×50 ml), and ethyl acetate (100 ml). The organic extracts were combined, dried over calcium sulfate, evaporated in vacuo, and purified by flash chromatography (SiO2, petrol/ether 1:1 v/v) to furnish a mixture of the title compound and 6-amino-2,4-di-bromophenol (0.600 g, of a 76:24 w/w mixture as judged by 1 H-NMR). Yield 6-amino-2-bromophenol, 43%.

Provenance & Evidence