Two-Phase Dibromocyclopropanation of Unsaturated Alcohols Using Flow Chemistry

Abstract

Dibromocyclopropanations are conventionally done by addition of dibromocarbene to alkenes under phase-transfer conditions in batch reactions using a strong base (50% NaOH (aq)), vigorous stirring and long reaction times. We have shown that cyclopropanation of unsaturated alcohols can be done under ambient conditions using continuous flow chemistry with 40% (w/w) NaOH (aq) as the base. The reactions were generally rapid; the yields were comparable to yields reported in the literature for the conventional batch reaction

Keywords

• dibromocyclopropanation
• CHBr₃
• Makosza reaction
• phase-transfer catalysis
• flow chemistry
• unsaturated alcohols