Acetic Acid → 2-Fluoro-5-nitroaniline

Participants

Reaction Steps

To a 500 ml Parr hydrogenation reactor were charged 8.1 g (0.0438 mole) of 2,4-dinitrofluorobenzene, 0.5 g of 5% palladium on carbon catalyst, 1.0 g (0.018 mole) of powdered iron, 150 ml of ethanol, 50 ml of glacial acetic acid, and 5 ml of water. The reaction was stopped after 152 psi of hydrogen had been absorbed. The reaction mixture was filtered, and the filtrate was evaporated under reduced pressure leaving a red solid. This solid was passed through a pad of silica gel, eluting with methylene chloride. The solvent was evaporated from the eluate, producing 5.85 g of crude 2-fluoro-5-nitroaniline, m.p. 94°-96° C. Analysis of the nmr spectrum of this material showed it to be >90% pure 2-fluoro-5-nitroaniline.

Provenance & Evidence