p-Nitrobenzyl bromide (CAS NO.: ), which is also known as 4-nitrobenzyl bromide, could be produced through the following synthetic routes.

In a 1-l. three-necked flask is placed 300 g. (2.2 moles) of technical p-nitrotoluene (m.p. 51–52°). The flask is fitted with a liquid-sealed stirrer, reflux condenser, and a separatory funnel arranged so that the stem reaches nearly to the bottom of the flask. The condenser is attached to a gas trap. The flask is heated in an oil bath at 145–150°, and 368 g. (118 cc., 2.3 moles) of bromine is added dropwise over a period of two hours.

After all the bromine has been added, the heating and stirring are continued for ten minutes. While still liquid, the contents of the flask are poured into a 5-l. round-bottomed flask containing 4 l. of hot ligroin (b.p. 90–100°), and 15 g. of Norite is added. The material is brought into solution by heating on an electric hot plate, and, after boiling for ten minutes, the solution is filtered rapidly with suction. After cooling to 20°, the crystals are filtered with suction, pressed thoroughly, and washed with two 50-cc. portions of cold ligroin. The crude product, m.p. 94–97°, weighs 280–315 g. (59–66 per cent of the theoretical amount) and is sufficiently pure for some purposes.

For purification, this material is dissolved in 3–3.5 l. of hot ligroin, boiled with 10–15 g. of decolorizing carbon, and filtered with suction. After cooling in an ice bath the crystals are collected on a Büchner funnel, pressed, and washed with two 25-cc. portions of cold ligroin. The pale yellow product melts at 97.5–99° and weighs 250–280 g. (53–59 per cent of the theoretical amount).