Nitrobenzene → Benzene, 1-bromo-3-nitro-

Participants

Reaction Steps

A vigorously stirred mixture consisting of 0.1 moles (5 ml) bromine-trifluoride and 0.12 moles (6.5 ml) of bromine was added into a brine cooled three-necked flask equipped with a magnetic stirrer and a condenser containing ca. 0.6-0.7 moles of nitrobenzene. The addition was carried out dropwise with vigorous stirring while the temperature was kept between zero and ten degrees centigrate. After the addition was completed the crude reaction mixture was poured into a stirred icy 5% sodium sulfite solution. The organic layer was separated, and the aqueous solution was extracted twice with two portions of 100 ml dichloromethane. The combined organic layer was washed with 5% sodium bicarbonate solution and successively with water. The organic phase was dried over anhydrous magnesium sulfate and the solvent evaporated. The crude reaction mixture was quantitatively analyzed by gas-chromatography internal standard program. The meta-bromonitrobenzene obtained was separated from the starting material by reduced pressure distillation. The yield of meta-bromonitrobenzene obtained, expressed in percentage of pure meta-bromonitrobenzene obtained based on reacted nitrobenzene, is 81%.

Provenance & Evidence