Trifluoroborane-methyl sulfide → HCID 69384518, compound

Participants

Reaction Steps

BF3—SMe2 (24 mL, 228 mmol) was added to a stirred solution of methyl[3,5-dibromo-4-(4-methoxyphenoxy)phenyl]acetate (2.5 g, 5.8 mmol) and dichloromethane (50 mL) at 0° C. The reaction mixture was stirred for 20 hours at room temperature and subsequently quenched with ice water (50 mL). The two layers were separated with a phase separator and the remaining water phase was extracted with ethyl acetate. Filtration through a silica pad gave the crude 3,5-dibromo-4-(4-hydroxyphenoxy)phenylacetic acid. The residue was dissolved in methanol (40 mL) and thionyl chloride (4 mL) was added carefully to the reaction. After 1.5 hours of heating at reflux, the organic phase was removed in vacuo and the residue was dissolved in chloroform. The organic phase was washed with water and concentrated to give methyl[3,5-dibromo-4-(4-hydroxyphenoxy)phenyl]acetate as beige solid (1.8 g, 75%).

Provenance & Evidence