Ethyl bromodifluoroacetate → Ethyl 4-(2-ethoxy-1,1-difluoro-2-oxoethyl)benzoate

Participants

Reaction Conditions

Reaction Steps

According to the Kumadaki method (supra) and the above-described scheme, ethyl 4-iodobenzoate (Compound 1d; 1.38 g, 5.0 mmol), bromodifluoroacetic acid ethyl ester (1.015 g, 5.0 mmol), copper powder (635.5 mg, 10.0 mmol) and DMSO (10 mL) were put into a two-neck reaction tube, and the mixture was stirred under argon atmosphere at 55° C. for 24 hours. The reaction mixture was extracted with ethyl acetate and washed with water, and an organic layer was dried with anhydrous sodium sulfate. Ethyl acetate was distilled away under reduced pressure, and by carrying out purification by silica gel column chromatography, 4-(2-ethoxy-1,1-difluoro-2-oxethyl)benzoic acid ethyl ester (Compound 2d) was obtained with a yield of 80%.

Provenance & Evidence