Dimethylformamide → 4'-(Methoxycarbonyl)-2'-methyl-[1,1'-biphenyl]-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A stirred solution of methyl 4-bromo-3-methylbenzoate (EP 0533268 A1) (1.0 g, 0.0044 mole) in dry DMF (10 ml) under argon was treated with 4-boronobenzoic acid (0.73 g, 0.0044 mole) and tetrakis (triphenylphosphine) palladium(0) (80 mg), followed by triethylamine (1.8 ml, 0.016 mole), the mixture was heated at 100° C. for 18 hours, then concentrated in vacuo. The residue was treated with ethyl acetate and extracted with 10% NaHCO3 solution. The basic extract was acidified with dil. HCl and extracted with ethyl acetate. The extract was dried (Na2SO4) and concentrated in vacuo to afford the title compound as a white solid (0.46 g, 39%).

Provenance & Evidence