Hydrogen Peroxide → N-(2-Bromo-4,5-dimethylphenyl)acetamide

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 50.0 g (0.41 mol) of 3,4-dimethylaniline in 250 mL of glacial acetic acid was added 46.0 g (0.45 mol) of acetic anhydride was added dropwise with ice-bath cooling. The reaction was heated for 15 minutes at 120° C., then cooled to 10° C. Bromine (32.8 g, 0.21 mol) was added dropwise over 25 minutes. The addition funnel was washed with a small amount of acetic acid, and 27.2 g (0.24 mol) of 30% hydrogen peroxide was added over 30 minutes. The reaction was stirred for 2 hours at 10°-15° C. and then poured into 1200 mL of cold water. The precipitated product was collected by filtration, washed with water, and dried under vacuum to give 93.0 g (94% yield) of crude 2-bromo-4,5-dimethylacetanilide which was used without further purification.

Provenance & Evidence