Hydrogen Bromide → Benzene, 1-bromo-3,5-dimethyl-

Participants

Reaction Steps

A solution of 42 g of sodium nitrite in 150 ml of water is added to a mixture, cooled to −5° C., of 200 ml of 48% HBr and 50 g of 3,5-dimethylaniline. The reaction mixture is stirred for 1 hour at from −5° C. to 0° C. Finally, this reaction mixture is slowly added to a mixture, heated to 80° C., of 88.3 g of copper(I) bromide and 150 ml of 48% HBr. The reaction mixture is stirred for 2 hours at 80° C. and observed by TLC monitoring (silica; hexane). When the reaction is complete, the product is obtained by water-vapour distillation and is purified by column chromatography (silica; hexane). In this manner, 1-bromo-3,5-dimethylbenzene was obtained in a yield of 60% (30 g).

Provenance & Evidence