4.5 Article

gem-Dibromomethyl Aromatics: Efficient Aldehyde Equivalents in the Knoevenagel-Doebner Reaction

Journal

SYNTHESIS-STUTTGART
Volume -, Issue 14, Pages 2349-2356

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0029-1216849

Keywords

Knoevenagel-Doebner reaction; tert-butyl cinnamates; gem-dibromomethyl aromatics; di-tert-butyl dicarbonate; hydrolytic

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A valuable variation of the Knoevenagel-Doehner reaction for the efficient synthesis of cinnamic esters is described. This reaction provides cinnamic esters in a single step from gem-dibromomethyl aromatics, which otherwise require the hydrolytic conversion of gem-dibromides into aldehydes, and demonstrates file use of an alternative reagent for noncommercial and expensive aldehydes. Further, the reaction of gem-dibromomethyl aromatics with malonic acid and di-tert-butyl dicarbonate for the one-pot synthesis of tert-butyl cinnamates is also described.

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