Acetic Anhydride → N-(4-fluoro-2-(trifluoromethyl)phenyl)acetamide

Participants

Reaction Steps

A solution of 4-fluoro-2-(trifluoromethyl)aniline (5.0 g, 27.91 mmol) in acetic anhydride (25 mL) was stirred at ambient temperature for 3 hours to produce a white needle precipitate. The reaction mixture was poured onto ice water, filtered then dried to give 6.0 g of N-[4-fluoro-2-(trifluoromethyl)phenyl]acetamide as an off-white solid which was used without further purification. The N-[4-fluoro-2-(trifluoromethyl)phenyl]acetamide (2.0 g, 9.04 mmol) was dissolved in concentrated H2SO4 (15 mL) and cooled to 0 degrees Centigrade using an ice bath. 70% HNO3 (1.5 mL) was added drop wise and the reaction stirred at 0 degrees Centigrade for 30 min and then at ambient temperature for 3 hours. The reaction mixture was poured onto ice-water, filtered then dried to give 2.4 g of the desired N-[4-fluoro-2-nitro-6-(trifluoromethyl)phenyl]acetamide.

Provenance & Evidence