Furfural → 2-(2,2-Dibromovinyl)furan

Participants

Reaction Conditions

Reaction Steps

A solution of carbon tetrabromide (241.6 g, 0.73 mol) in anhydrous DCM (1000 mL) was cooled to −20° C. under nitrogen and triphenylphosphine (191.1 g, 0.73 mol) in anhydrous DCM (1000 mL) was added drop wise. After twenty minutes of stirring, the reaction was cooled to −60° C., and then a mixture of furfural (30 mL, 0.36 mol) and triethylamine (50.5 mL, 0.36 mol) in anhydrous DCM (375 mL) were added drop wise. The mixture was brought to room temperature and diethyl ether (500 mL) was added with stirring. The reaction was filtered and filtrate was concentrated in vacuo. Column chromatography (SiO2, heptanes) yielded the title compound (58.1 g, 63%) as a brown oil:

Provenance & Evidence