Dichloromethane → Benzoic acid, 2-chloro-5-cyclopropyl-, ethyl ester

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In a schlenck tube, a mixture of ethyl 5-bromo-2-chlorobenzoate (7.60 mmol, 2 g), 2-cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (7.59 mmol, 1.3 g), Cs2CO3 (18.97 mmol, 6.18 g), PdCl2dppf.CH2Cl2 (0.76 mmol, 0.620 g) in dioxane (70 ml) and water (15 ml) was heated for 2 hours at 110° C., under argon atmosphere. The solvent was evaporated and the mixture was extracted between ethyl acetate and water. The crude mixture was purified by chromatography over SiO2 eluting hexane/ethyl acetate mixtures and affording 1.5 g (yield 92%) of the expected product.

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