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Journal of the Brazilian Chemical Society

Print version ISSN 0103-5053On-line version ISSN 1678-4790

Abstract

FERREIRA, Misael; FERNANDES, Luciano  and  SA, Marcus M.. A highly efficient and general method for the preparation of (Z)-allylic bromides derived from Morita-Baylis-Hillman adducts. J. Braz. Chem. Soc. [online]. 2009, vol.20, n.3, pp.564-568. ISSN 0103-5053.  http://dx.doi.org/10.1590/S0103-50532009000300023.

(Z)-2-(Bromometil)-2-alcenoatos são importantes intermediários sintéticos e foram preparados de forma simples e prática pelo tratamento de α-metileno-β-hidroxiésteres (produtos da reação de Morita-Baylis-Hillman) com LiBr/H2SO4 em acetonitrila à temperatura ambiente. Além de fornecer altos rendimentos e de tolerar a presença de diversos grupos funcionais, esta nova metodologia utiliza reagentes baratos e não faz uso de HBr.

Keywords : Morita-Baylis-Hillman reaction; α-methylene-β-hydroxyesters; (Z)-allylic bromides; N-allyl acetamides.

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