2-Fluoro-5-nitroaniline

70-34-8

369-36-8

The general procedure for the synthesis of 2-fluoro-5-nitroaniline from 2,4-dinitrofluorobenzene is as follows: 18.61 g (0.10 mol) of 2,4-dinitrofluorobenzene, 0.5 g of 5% palladium-carbon catalyst, 100 mL of glacial acetic acid, and 100 mL of anhydrous ethanol were added to a 500 mL Parr hydrogenation unit. The device was equipped with a thermocouple and a cooling jacket. During the reaction, the temperature of the reaction mixture was maintained at 20-25°C, the hydrogen pressure was maintained at 370 psi, and the reaction time was 2.5 hours. Upon completion of the reaction, the reaction mixture was poured into 400 mL of water. It was extracted twice with 200 mL of dichloromethane, the organic phases were combined and dried over anhydrous magnesium sulfate. The solvent was removed by concentration under reduced pressure and the resulting residue was filtered through a silica gel pad and eluted with dichloromethane. The eluate was concentrated again under reduced pressure and the residue was further purified by column chromatography using dichloromethane:heptane (80:20, v/v) as eluent. Finally, the solvent was evaporated under reduced pressure to give 2.75 g of 2-fluoro-5-nitroaniline in 17.6% yield.