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Synthesis 2009(14): 2349-2356
DOI: 10.1055/s-0029-1216849
DOI: 10.1055/s-0029-1216849
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
gem-Dibromomethyl Aromatics: Efficient Aldehyde Equivalents in the Knoevenagel-Doebner Reaction
Further Information
Received
3 March 2009
Publication Date:
29 May 2009 (online)
Publication History
Publication Date:
29 May 2009 (online)
![](https://www.thieme-connect.de/media/synthesis/200914/lookinside/thumbnails/10.1055-s-0029-1216849-1.jpg)
Abstract
A valuable variation of the Knoevenagel-Doebner 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 the 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.
Key words
Knoevenagel-Doebner reaction - tert-butyl cinnamates - gem-dibromomethyl aromatics - di-tert-butyl dicarbonate - hydrolytic
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