A general synthesis of 2'-hydroxychalcones from bromomagnesium phenoxides and cinnamic aldehydes

Abstract A highly selective synthetic route of general utility was devised for the preparation of 2'-hydroxychalcones 4 . The procedure involves the regiochemical controlled reaction between bromomagnesium salts of mono and dihydric phenols 1 and variously substituted cinnamaldehydes 2 in aprotic apolar media and in the presence of a suitable basic additive. Application of this procedure to some naturally occurring chalcones is reported. The crucial role of the additive is also emphasized.