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

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.

1. temperatureunder reflux for 6 hours
2. customthe solvent was removed by evaporation under reduced pressure
3. additionEthyl acetate was added to the residue
4. washthe resulting solution was washed with water
5. dry with materialdried over sodium sulfate
6. customThe solvent was removed by evaporation under reduced pressure
7. customthe resulting residue was purified by column chromatography through silica gel using
8. additiona mixture of hexane and ethyl acetate as the eluent
9. additionby volume mixture of the two solvents

ORD record

ord-07be19fe31684880a00f0f7417ce46f1

Source dataset

uspto-grants-1998_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05736487