Dimethyl Sulfoxide → 4'-Formyl-[1,1'-biphenyl]-2-carbonitrile

Participants

Reaction Steps

53 ml of oxalyl chloride in 2 litres of methylene chloride are cooled to -60°. A solution of 88 ml of dimethyl sulfoxide in 150 ml of methylene chloride is added dropwise at this temperature and the mixture is then stirred for 2 minutes. After this, 117 g of 4-hydroxymethyl-2'-cyanobiphenyl in 1 litre of methylene chloride are added dropwise at -60°. After addition has ended (about 5 minutes), the mixture is subsequently stirred for 15 minutes. After this, 390 ml of triethylamine are added dropwise. The mixture is then stirred at -60° for 2 minutes and allowed to wann to room temperature. The reaction mixture is poured into water, extracted with methylene chloride, and the organic phase is washed with dilute hydrochloric acid and brine, dried and concentrated. The product is stirred in hexane, filtered off with suction, washed and dried at 600 in a high vacuum. Elemental analysis: C 80.7%, H 4.5%, N 6.7%, O 7.7%.

Provenance & Evidence