2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl → (5-Methoxybenzofur-7-yl)acetic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

Dissolve 7-bromo-5-methoxybenzofuran (6.0 g, 26.43 mmol), bis(dibenzylideneacetone)palladium (1.32 g, 2.3 mmol) and 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (2.7 g, 6.86 mmol) in anhydrous tetrahydrofuran (36 mL), add freshly prepared 2-ethoxy-2-oxoethylzinc bromide in tetrahydrofuran (66 mL). Heat at 50-60° C. for 5 h. Cool and filter mixture through celite and evaporate to a thick red-brown oil (30 g). Purify by flash chromatography using a gradient of ethyl acetate in hexanes yields the pure compound as a thick yellow oil (6.2 g, quant). ESMS m/z (relative intensity) 235.2 (M++H+, 10), 161.1 (M+−CO2Et+H+, 100).

Provenance & Evidence