Hydrochloric Acid → 3-Bromo-4-chloroaniline

Participants

Reaction Conditions

Reaction Steps

A mixture of iron (17.9 g), ethanol (120 ml), water (80 ml) and conc. hydrochloric acid (1.5 ml) was heated to 70° C., this temperature was maintained during the addition of 1-chloro-2-bromo-4-nitrobenzene (21.0 g) in ethanol (100 ml) over 25 min. The mixture was heated to reflux for 11/4 hours before adjusting the pH to 9-10 with sodium hydroxide solution. The mixture was filtered hot through Hyflo™ washing with hot ethanol and water. The mixture was concentrated, dichloromethane added and the organic solution washed with water then dried (MgSO4). The product was purifed by silica gel chromatography then recrystalised from ether/hexane to give the sub-title compound as a solid.

Provenance & Evidence