2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl → Ethyl 6-(acetylamino)-4'-(benzyloxy)-2',6'-dimethylbiphenyl-3-carboxylate

Participants

Reaction Steps

[4-(Benzyloxy)-2,6-dimethylphenyl]boronic acid (333 mg, 1.30 mmol) and ethyl 4-(acetylamino)-3-bromobenzoate (286 mg, 1.00 mmol) were dissolved in a mixture of 2 M aqueous sodium carbonate solution (1.30 mL), toluene (10 mL) and 1,2-dimethoxyethane (1 mL), the air was substituted with argon gas, and dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (65.7 mg, 0.16 mmol) and tris(dibenzylideneacetone)dipalladium(0) (36.6 mg, 0.04 mmol) were added. The reaction mixture was heated under reflux under an argon atmosphere for one day. After cooling the reaction mixture, brine was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=9/1-hexane/ethyl acetate=13/7) to give the title compound (401 mg, yield 96%) as a colorless amorphous powder.

Provenance & Evidence