Potassium Carbonate → 3-[2-(2-Benzyloxy-5-chlorophenyl)cyclopent-1-enyl] benzoic acid ethyl ester

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Reaction Steps

A mixture of 1,2-dibromocyclopentene (1.72 g, 7.6 mmol), 2-benzyloxy-5-chlorophenylboronic acid (500 mg, 1.9 mmol), potassium carbonate (2.1 g, 15.2 mmol) and tetrakis (triphenyl phosphine)palladium(0) (220 mg, 0.19 mmol) was stirred and heated in 1:1 toluene/ethanol (15 ml) at 90° C. under nitrogen for 2 hours. After cooling the mixture was diluted with diethyl ether/water and the organic phase dried (magnesium sulphate), evaporated to dryness and the residue purified by chromatography on silica (2% ethyl acetate in iso-hexane then 10% dichloromethane in iso-hexane) to yield the title compound as a white solid (427 mg, 62%). 1H NMR (CDCl3) δ:1.99–2.07 (2H, m), 2.67–2.72 (2H, m), 2.76–2.81 (2H, m), 5.06 (2H, s), 6.85 (1H, d, J=9 Hz), 7.17–7.38 (7H, m).

Provenance & Evidence