Bromobenzene → Biphenyl

Participants

Reaction Steps

A mixture comprising 4 parts of sodium diisopropyl naphthalene sulphonate, 1.2 parts of 3% palladium on carbon catalyst, 20 parts of sodium hydroxide, 80 parts of water, 6.8 parts of sodium formate and 15.7 parts of bromobenzene is stirred and heated for 4 hours under reflux. The mixture is then allowed to cool to 90°, a further charge of 6.8 parts of sodium formate is added, and the mixture is reheated and stirred under reflux for a further 16 hours. The mixture is then steam distilled until 800 parts of distillate are collected. The distillate is extracted with chloroform and the chloroform solution, is shown by gas chromatography to contain benzene and biphenyl but no bromobenzene. The chloroform solution is then concentrated by distillation, yielding 5.01 parts of biphenyl, melting at 69°-70°.

Provenance & Evidence