4-Bromo-3-methoxyaniline → 4-Bromo-3-methoxyphenol

Participants

Reaction Steps

3-Methoxy-4-bromoaniline (D1) (10.0 g, 49 mmoles) in water (60 ml) and concentrated sulphuric acid (30 ml) was treated with a solution of sodium nitrite (3.4 g, 49 mmoles) in water (15 ml) dropwise keeping the temperature below 5° C. The resulting slurry was then added slowly to a mixture of water (60 ml) and concentrated sulphuric acid (30 ml) at 80° C. and stirred at this temperature for 3 hrs. The mixture was cooled and extracted with dichloromethane (2×200 ml). The organics were then extracted with 2N sodium hydroxide solutions (2×100 ml). The aqueous was washed with more dichloromethane (2×200 ml) then acidified to pH 1. Extraction with dichloromethane, drying (Na2SO4) and evaporation to dryness gave the title compound (D8) (6.95 g, 69%).

Provenance & Evidence