Hydrochloric Acid → 2-But-1-enyl-5-(4'-ethyl-2,3-difluorobiphenyl-4-yl)selenophene

Participants

Reaction Steps

4.8 g (12.0 mmol) of propyltriphenylphosphonium bromide are initially introduced together with 3.60 g (9.56 mmol) of 5-(4′-ethyl-2,3-difluoro-biphenyl-4-yl)selenophene-2-carbaldehyde in 180 ml of THF, and a solution of 1.30 g (11.6 mmol) of potassium tert-butoxide in 20 ml of THF is added with ice-cooling. The mixture is stirred at RT for 1 h. Water and 2 N hydrochloric acid are added, and the batch is extracted with MTBE. The organic phase is washed with sat. sodium chloride soln. and dried using sodium sulfate. The solution is concentrated to dryness, and the residue is purified by column chromatography (SiO2, n-heptane:toluene=95:5). 2-But-1-enyl-5-(4′-ethyl-2,3-difluorobiphenyl-4-yl)selenophene is obtained as a yellow solid.

Provenance & Evidence