4-Bromotoluene → 1-(4'-Chlorobiphenyl-4-yloxy)-4-methylbenzene

Participants

Reaction Conditions

Reaction Steps

Potassium t-butoxide (20 g) was added to a solution of 4-chloro-4'-hydroxybiphenyl (mp 142° C., prepared as in J.A.C.S, 2219, 1964) (33 g) in methanol (200 ml). The resulting mixture was evaporated to dryness under reduced pressure and the solid residue obtained was mixed with p-bromotoluene (83 g), copper powder (1 g) and dimethylsulphoxide (80 ml). The resulting mixture was refluxed (190° C.) for 16 hours, potassium hydroxide (9 g) was added and the mixture was refluxed for a further 6 hours. After cooling, the mixture was poured into water and extracted with methylene chloride. The methylene chloride extract was washed with water, dried (MgSO4) and evaporated to give a crude product in the form of an oil which solidified on standing. This crude product was triturated with 60/80 petroleum ether to give 1-(4'-chlorobiphenyl-4-yloxy)-4-methylbenzene (10 g, 29%) mp 130° C.

Provenance & Evidence