Rapid and Stereoselective Conversion of a trans-Cinnamic Acid to a beta-Bromostyrene

Thomas A. Evans
Department of Chemistry and Biochemistry, Denison University, Granville, OH 43023
J. Chem. Educ., 2006, 83 (7), p 1062
DOI: 10.1021/ed083p1062
Publication Date (Web): July 1, 2006

Abstract

The stereoselective synthesis of an aryl vinyl bromide is accomplished in a rapid microscale reaction of trans-4-methoxycinnamic acid with N-bromosuccinimide in dichloromethane. The product is purified by dry column vacuum chromatography and its stereochemistry is determined by 1H NMR. TLC, GC and GC–MSD can also be used. This guided-inquiry experiment links reactivity, stereochemistry, and mechanism in electrophilic addition reactions of alkenes and in E1 and E2 elimination reactions that form alkenes.

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History

  • Received: August 03, 2009

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