Acetic Acid → n-(2-Fluoro-4-hydroxyphenyl)acetamide

Participants

Reaction Steps

373.3 mg of iron powder were added to a solution of 300 mg of 3-fluoro-4-nitrophenol [prepared as described in step (c) above] in 6 ml of glacial acetic acid. The resulting mixture was stirred under reflux for 6 hours, after which it was allowed to cool to room temperature. Ice-water was then added to the reaction mixture and the solvent was removed by evaporation under reduced pressure. Ethyl acetate was added to the residue and the resulting solution was washed with water and then dried over sodium sulfate. The solvent was removed by evaporation under reduced pressure and the resulting residue was purified by column chromatography through silica gel using a mixture of hexane and ethyl acetate as the eluent, initially using a 2:1 by volume mixture of the two solvents and then changing to a 1:1 by volume mixture, to give 206.8 mg (yield 64%) of the title compound as a brown solid.

Provenance & Evidence