4-Nitrobenzyl fluoride (CAS NO.: ), which is also known as nzene, 1-(fluoromethyl)-4-nitro-, could be produced through the following synthetic route.

A dry, 1-l., three-necked, round-bottomed flask is fitted with a 500-ml. dropping funnel, thermometer, a magnetic stirrer, and a reflux condenser protected from the atmosphere with a drying tube. The apparatus is flushed with dry nitrogen, and 150 ml. of dry dichloromethane and 21 ml. (0.16 mole) of diethylaminosulfur trifluoride are added to the flask. The contents of the flask are cooled to 10°, and a solution of 23.0 g. (0.150 mole) of 4-nitrobenzyl alcohol in 450 ml. of dichloromethane is added dropwise at a fast rate (45 minutes). The reaction mixture is allowed to come to room temperature and poured into a beaker containing 300 g. of ice, decomposing any unreacted diethylaminosulfur trifluoride. The organic layer is separated, and the water layer is extracted twice with 45-ml. portions of dichloromethane. The organic layer and extracts are combined, washed with 150 ml. of water, and dried over anhydrous magnesium sulfate. Evaporation to dryness under reduced pressure gives 20.9–22.1 g. (90–95%) of crude product. Recrystallization from 500 ml. of pentane yields 15.5 g. (67%) of 4-nitrobenzyl fluoride as colorless needle-shaped crystals, m.p. 36–37°.

Notice: Protective gloves should be worn when handling diethylaminosulfur trifluoride because this material can cause severe HF burns.