Dimethyl Sulfoxide → 3-(2-Bromo-6-nitrophenyl)-2-propenenitrile

Participants

Reaction Steps

After stirring 2-bromo-6-nitrobenzaldehyde (30.4 g), magnesium oxide (75 g) and dimethyl sulfoxide (11.3 ml) sufficiently for 1 minute, diethyl (cyanomethyl)phosphonate (25.8 ml) was added thereto and the mixture was stirred for further 2 hours. After the completion of stirring, the mixture was left stand overnight. Then, ethyl acetate was added thereto, and the mixture was stirred and then filtered. The filtrate was concentrated and the residue was purified by silica gel column chromatography (ethyl acetate), to give 32 g of 3-(2-bromo-6-nitrophenyl)-2-propenenitrile (E-isomer:Z-isomer=3:1).

Provenance & Evidence