Acetic Anhydride → N-(4-Bromo-5-fluoro-2-methylphenyl)acetamide

Participants

Reaction Steps

A solution of 5-fluoro-2-methylaniline (24A, 25 g, 200 mmol) in toluene (250 mL) was treated with acetic anhydride (25 mL 226 mmol) heated at reflux for 1 hour. The reaction mixture was cooled when a colorless solid precipitated out which was filtered and washed with a mixture of ether and hexanes. The colorless solid was taken in acetic acid (150 mL) and treated dropwise with a solution of bromine (9.6 mL, 186 mmol) in acetic acid (20 mL) and stirred at rt. for 12 hours. The solution was diluted with water and the solid separating out was filtered and washed to yield N-(4-bromo-5-fluoro-2-methylphenyl)acetamide (24B, 40 g) as a colorless solid.

Provenance & Evidence