Sulfuric Acid → 3-Cyano-4-fluorobenzoic acid

Participants

Reaction Steps

To a mixture of 2-fluoro-5-methylbenzonitrile (13.5 g, 0.1 mol), tetrabutylammonium bromide (1.61 g, 5 mmol), and ruthenium(III)chloride trihydrate (0.261 g, 1 mmol) in dichloromethane (150 mL) was added a solution of sodium hypochlorite (645 mL, 0.45 mol) which had been neutralized to pH 9 with 20% sulfuric acid. The reaction mixture was stirred and maintained at pH 9 by adding 20% sodium hydroxide solution at RT. After 3 h, the aqueous phase was separated and neutralized to pH 2 with 20% sulfuric acid and the solid which formed was filtered to give the title compound (3.4 g, 20%). mp 177-8° C. 1H NMR (CDCl3) δ 7.35 (t, J=8.70 Hz, 1H), 8.38 (m, 1H), 8.42 (m, 1H).

Provenance & Evidence