Water → 2-Hydroxy-5-(4'-hexylbiphenyl-4-yl)thiophene

Participants

Reaction Steps

A 1M solution of boron tribromide in dichloromethane (50 cm3) is added dropwise to a solution of 2-propyloxy-5-(4′-hexylbiphenyl-4-yl)thiophene [Zh. Org. Khim., (1979) Vol. 49, pp. 476] (1.0 g) and dichloromethane (50 cm3) at 0° C. under an atmosphere of nitrogen. The reaction solution is stirred overnight and water (100 cm3) added. The organic layer is separated off and the aqueous layer extracted with dichloromethane (2×100 cm3). The combined organic layers are washed with brine (2×100 cm3) and then dried (MgSO4), filtered and evaporated down. The residue is purified by column chromatography on silica gel using a 9:1 hexane/ethyl acetate mixture as eluent and recrystallisation from ethanol to yield 0.4 g of g 2-hydroxy-5-(4′-hexylbiphenyl-4-yl)thiophene.

Provenance & Evidence