Water → 2-Cyclopropyl-5-ethoxy-2',4'-difluorobiphenyl-4-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo-5-ethoxy-2′,4′-difluorobiphenyl-4-carbaldehyde (5.70 g), cyclopropylboronic acid (2.15 g), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (549 mg), tris(dibenzylideneacetone)dipalladium (0) (612 mg) and 2 M aqueous sodium carbonate solution (25.1 mL) in toluene (50 mL) was stirred at 100° C. for 2 hours under nitrogen atmosphere. The mixture was poured into water at room temperature and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over anhydrous magnesium sulfate. Activated carbon (600 mg) was added to the filtrate. The mixture was stirred for 20 minutes at room temperature. After filtration, the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (hexane/ethyl acetate) to give the title compound (4.62 g).

Provenance & Evidence