2-FLUORO-4-NITROBENZONITRILE

350-32-3

34667-88-4

General procedure for the synthesis of 2-fluoro-4-nitrobenzonitrile from 2-fluoro-4-nitrobenzamide: A mixture of 2-fluoro-4-nitrobenzamide (0.83 g, 4.6 mmol) and phosphorus pentoxide/hexamethyldisiloxane in 1,2-dichloroethane (20 mL) was heated and refluxed for 4 hr at 100 °C under nitrogen atmosphere. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently filtered through a silicone plug, washed first with hexane (200 mL) and then with 5% methanol/chloroform mixture (400 mL). The methanol/chloroform washings were combined and concentrated under reduced pressure to give 2-fluoro-4-nitrobenzonitrile (0.71 g, 95% yield) as a beige solid.1H NMR (DMSO-d6) data were as follows: δ 8.46 (dd, J = 9.5, 2.0 Hz, 1H), 8.37-8.22 (m, 2H).