Hydrochloric Acid → tert-butyl 3-[4'-(2-Carboxy-ethyl)-biphenyl-4-yl]-propionate

Participants

Reaction Conditions

Reaction Steps

Tert-butyl 3-(4-bromophenyl)propionate (433 mg, 1.52 mmol) in acetonitrile-water (3:1, 13 ml) under argon atmosphere was treated with 4-(2-carboxyethyl)benzeneboronic acid (294 mg, 1.52 mmol), K2CO3 (251 mg, 1.82 mmol) and (Ph3P)4Pd (87 mg, 73 μmol), and the stirred mixture was heated at 90° C. for 4 hours. Excess ethyl acetate and 2 M HCl was added and the organic phase was washed with 2×2 M HCl and 2× water. Drying over MgSO4 and evaporation in vacuo gave the crude product, which was purified by chromatography on silica column eluted with ethyl acetate/hexane/acetic acid 50:50:1 to provide tert-butyl 3-[4′-(2-Carboxy-ethyl)-biphenyl-4-yl]-propionate, 330 mg (62%).

Provenance & Evidence