Water → 4-Fluoro-2-methylbenzoic acid

Participants

Reaction Steps

A solution of 4-fluoro-2-methyl-benzonitrile (5.0 g, 37 mmol), H2SO4 (20 mL) and H2O (15 mL) was stirred at 80° C. for 17 h. The reaction mixture was cooled to ambient temperature and intermediate carboxamide collected as a precipitate. The material was used without purification. The intermediate carboxamide (5.7 g) was treated with 85% phosphoric acid (20 mL) and stirred at 150° C. for 18 h. After this time, the reaction mixture was cooled to ambient temperature and treated with water (30 mL). The resulting solution was extracted with ethyl acetate (2×200 mL). The combined organic extracts were dried over anhydrous MgSO4, filtered, and concentrated to afford 4-fluoro-2-methyl-benzoic acid. The material was without further purification.

Provenance & Evidence