Water → (RS)-5-Benzyloxy-2-bromomethyl-2,3-dihydro-benzofuran

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Reaction Steps

(RS)-Acetic acid 4-benzyloxy-2-(2,3-dibromo-propyl)-phenyl ester (5.05 g, 11.3 mmol) was suspended in EtOH (50 ml) and sodium methoxide (620 mg, 11.3 mmol) added and the mixture stirred for 2 hr at ambient temperature. Distilled H2O (100 ml) and CH2Cl2 (100 ml) was then added and the organic phase separated. The aqueous phase was extracted with CH2Cl2 (100 ml) and the combined organic extracts washed with satd. NaCl solution (100 ml). After drying with Na2SO4, filtration and evaporation a yellow oil resulted which was chomatographed over SiO2 (Merck 230-400 mesh) with CH2Cl2 to afford 5-benzyloxy-2-(RS)-bromomethyl-2,3-dihydro-benzofuran as a yellow oil (3.0 g, 9.39 mmol, 83%), MS: m/e=318.0 (M+).

Provenance & Evidence