Hydrochloric Acid → Ethyl 4-Amino-2-fluorobenzoate

Participants

Reaction Conditions

Reaction Steps

A solution of 2-fluoro-4-nitro-benzoic acid ethyl ester (725 mg, 3.4 mmol) in tetrahydrofuran (11 ml) was treated with tin metal (807 mg, 6.8 mmol, 2 equiv.) and 6N HCl (5.4 ml). The mixture was warmed to 50° C. and stirred for 30 min. After cooling to room temperature, the solvent was evaporated. The residue was cooled to 0° C. and treated with 10% NaOH (20 ml). After stirring for a few minutes, the suspension was filtered, washing with water. The solid was dissolved in tetrahydrofuran and treated with Na2SO4. Filtration and evaporation of the solvent yielded a light yellow solid, which was purified by trituration in diisopropylether. 4-Amino-2-fluorobenzoic acid ethyl ester was obtained as a light yellow solid, 554 mg (89% yield), MS (ISP): m/e=184.1 (M+H+).

Provenance & Evidence