Benzaldehyde → Ethyl 2,2-difluoro-3-hydroxy-3-phenylpropanoate

Participants

Reaction Conditions

Reaction Steps

A mixture of 48 g of ethyl bromodifluoroacetate, 4.5 g of dibromoethane and 50 g of tetrahydrofuran was added dropwise to a mixture of 15 g of zinc, 21 g of benzaldehyde, 60 mL of trimethyl borate, and 50 g of tetrahydrofuran at a temperature of 60° C., followed by stirring for 10 hours at 90° C. Thereafter, 100 g of 10 wt % hydrochloric acid was added to quench the reaction. By filtration, the insoluble was removed, and the filtrate was washed with saturated sodium chloride water. The reaction solution after washing was concentrated under reduced pressure. The concentrate was purified by distillation, obtaining 28 g of the target compound, ethyl 2,2-difluoro-3-hydroxy-3-phenylpropionate as colorless oily matter (yield 60%).

Provenance & Evidence