Nitric Acid → 3-Bromo-4-nitrophenol

Participants

Reaction Steps

To a solution of 3-bromophenol (10 g) in chloroform (50 ml) and acetic acid (50 ml) was added 70% nitric acid (60 ml) dropwise on an ice bath, and the solution was stirred for 1 hour. The reaction mixture was poured into ice water, extracted with ethyl acetate, then sequentially washed with a saturated aqueous solution of sodium bicarbonate, water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (4.1 g) and 5-bromo-2-nitrophenol (1.8 g).

Provenance & Evidence