Toluene → 2'-formylbiphenyl-2-carbonitrile

Participants

Reaction Steps

The boron compound (24) (65.6 g) and 2-bromobenzonitrile (84 g) were placed into a 3 liter 3-neck flask fitted with a mechanical stirrer containing 20 g of tetrakis(triphenylphosphine)palladium(0), 1 liter of toluene, 480 ml of 2M sodium carbonate solution and 240 ml ethanol. The mixture was gently refluxed under argon with rapid stirring for 24 hours. A further 3 g of triphenylphosphine was added and the mixture was continued to reflux overnight. While it was still warm 200 ml of water and 300 ml of tetrahydrofuran was added to the mixture. The organic layer was separated while warm, and the aqueous layer was extracted with ethyl acetate. The organic extracts were combined and dried (MgSO4). The solid material was recrystallized from a mixture of ethyl acetate and methylene chloride, to yield 55 g of 2-formyl-2'-cyanobiphenyl (99+% pure).

Provenance & Evidence