Acetic Anhydride → 2-Acetylamino-6-fluorophenol

Participants

Reaction Steps

In 290 ml of acetic acid were dissolved 26.4 g (0.168 mole) of 2-fluoro-6-nitrophenol and 17.2 g (0.168 mole) of acetic anhydride, and 3.0 g of 5% palladium carbon was added thereto. Hydrogen gas was passed through the mixture, with stirring, at room temperature for 2 hours. After the reaction mixture had been filtered and the filtrate concentrated under reduced pressure, the residue was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was applied to silica gel column chromatography (the eluent used was a mixture of ethyl acetate:toluene=1:2) to obtain 25.9 g of 2-acetylamino-6-fluorophenol as brown crystals.

Provenance & Evidence