Synthesis and reactions of (E)- and (Z)-1,3-dibromo-2-methoxypropene

(Z)-1,3-Dibromo-2-methoxypropene is prepared in 90% yield by dehydrohalogenation of 1,2,3-tribromo-2-methoxypropane with diisopropylamine in dichloromethane. The E-isomer can be obtained as the only product in almost quantitative yield by UV irradiation of the Z-isomer. Nucleophilic displacement reactions of the allylic bromide and palladium-catalyzed coupling reactions of the vinylic bromide in (E)- and (Z)-1,3-dibromo-2-methoxypropene have been studied.