Palladium on charcoal-catalysed arylation of methyl vinyl ether with 4-bromonitrobenzene

Abstract

Palladium on charcoal has been used as a catalyst in the reaction of 4-bromonitrobenzene with methyl vinyl ether to give 81% of the desired (E)- and (Z)-methyl 2-p-nitrophenylvinyl ether. In addition, methyl 1-p-nitrophenylvinyl ether, isolated as 4-nitroacetophenone, was formed in 10% yield. The dependence of these yields on solvent, temperature, and reaction time has been studied. Reaction in toluene at 120 °C for 16 h in the presence of triethylamine gave the best results. The E to Z ratios were approximately constant.