Sulfuric Acid → 3-Bromo-5-nitrobenzonitrile

Participants

Reaction Steps

To a stirring mixture of 1.2 g (4.96 mmol) of 2-amino-3-bromo-5-nitrobenzonitrile and 2.8 mL of H2SO4 in 28 mL of EtOH at 90° C. was added 2.5 g (36.2 mmol) of NaNO2 in several portions. After 13.5 h, EtOAc and H2O were added. The organic layer was washed with H2O and brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (5% EtOAc/hexanes) provided 927 mg of 3-bromo-5-nitrobenzonitrile in 82% yield as a yellow solid.

Provenance & Evidence