Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → (E)-ethyl 3-(5-bromo-2-chloropyridin-3-yl)acrylate

Participants

Reaction Steps

A vial was charged with 5-bromo-2-chloronicotinaldehyde (500 mg, 2.268 mmol, Small Molecules, Inc.) and THF (9072 μl). (Carbethoxymethylene)triphenylphosphorane (830 mg, 2.381 mmol) was added to the solution, and the mixture was stirred at RT for 1.5 h. The crude mixture was loaded onto silica gel and purified using a gradient of 0-50% EtOAc/heptane to provide (E)-ethyl 3-(5-bromo-2-chloropyridin-3-yl)acrylate (660 mg, 2.272 mmol, 100% yield) as a white solid. m/z (ESI) 291.8 (M+H)+.

Provenance & Evidence