Ethanol → Ethyl 4-fluoro-3-nitrobenzoate

Participants

Reaction Steps

4-Fluoro-3-nitrobenzoic acid (5.3 g, 0.029 mol), ethanol (15 mL, 0.26 mol), toluene (40 mL, 0.4 mol) and sulfuric acid (1.75 mL, 0.0328 mol) were added to a 100 mL round-bottomed flask fitted with a Dean Stark trap and reflux condenser. The reaction mixture was heated with stirring under nitrogen to reflux and maintained at reflux for 5 hours. The reaction mixture was concentrated to about half volume diluted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, water and dried over sodium sulfate. Concentration yielded a straw colored oil (5.68 g, 93%), which was used in the next step without further purification.

Provenance & Evidence