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Short Reports • J. Braz. Chem. Soc. 20 (3) • 2009 • https://doi.org/10.1590/S0103-50532009000300023   copy

A highly efficient and general method for the preparation of (Z)-allylic bromides derived from Morita-Baylis-Hillman adducts

Authorship SCIMAGO INSTITUTIONS RANKINGS

Representative (Z)-2-(bromomethyl)-2-alkenoates were easily prepared in high yield by treating α-methylene-β-hydroxyesters (Morita-Baylis-Hillman adducts) with LiBr/H2SO4 in acetonitrile at room temperature. Besides the tolerance to many diverse functional groups, this new methodology employs inexpensive reagents and avoids the use of HBr.

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

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