Sulfuric Acid → 2-bromo-6-methoxy-4-nitroaniline

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo-6-methoxy-4-nitroaniline, as described above in Step A, (450 mg, 1.82 mmol) in water (40 mL) was cooled to 0° C. and treated with sulfuric acid (1.1 mL) followed by a solution of sodium nitrite (125 mg, 1.82 mmol) in water (0.5 mL) via pipet over 5 minutes. After stirring for 45 minutes at 0° C., the reaction was treated with ice cold 50% H3PO2 (10 mL) and stirred for 1.5 hours at 0° C. The reaction was quenched by adding aqueous saturated NaHCO3, filtered and dried overnight sitting in the hood to give an orange solid. This material was purified by column chromatography (5:1 hexane:ethyl acetate) to give 2-bromo-6-methoxy-4-nitroaniline and 3-bromo-5-nitroanisole as an off-white solid.

Provenance & Evidence