Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl 3-(5-Bromo-2-pyridyl)acrylate

Participants

Reaction Steps

5-Bromopyridine-2-carbaldehyde (502 mg, 2.70 mmol) was added to a solution of ethyl (triphenyl-λ5-phosphanylidene)acetate (1570 mg, 4.51 mmol) in DMF (5.00 mL) and the reaction mixture was stirred at room temperature for 40 minutes. The mixture was poured into ice-water, and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated under reduced pressure. A mixture of hexane:ethyl acetate (2:1) was added to the crude residue and the insoluble materials were filtered off. The filtrate was concentrated under reduced pressure and purified by silica gel chromatography (4% ethyl acetate in hexanes) to afford ethyl-3-(5-bromopyridin-2-yl)prop-2-enoate MS APCI calc'd for C10H11BrNO2 [M+H]+ 256 and 258. found 256 and 258.

Provenance & Evidence