Sodium Carbonate → 4-(Benzyloxy)-2'-fluoro-5'-methoxy-[1,1'-biphenyl]-3-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(benzyloxy)-5-bromobenzaldehyde (5.00 g) in toluene (70 mL) were added (2-fluoro-5-methoxyphenyl)boronic acid (4.40 g), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (710 mg), tris(dibenzylideneacetone)dipalladium(0) (790 mg) and 2.0M aqueous sodium carbonate solution (25.8 mL) at room temperature, and the mixture was stirred at 100° C. for 1 hr. The reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (4.00 g) as orange crystals.

Provenance & Evidence