Tetrahedron

Halogen–lithium exchange between substituted dihalobenzenes and butyllithium: application to the regioselective synthesis of functionalized bromobenzaldehydes

M Dąbrowski, J Kubicka, S Luliński, J Serwatowski

Index: Dabrowski, Marek; Kubicka, Joanna; Lulinski, Sergiusz; Serwatowski, Janusz Tetrahedron, 2005 , vol. 61, # 27 p. 6590 - 6595

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Citation Number: 29

Abstract

Halogen–lithium interconversion reactions between unsymmetrically substituted mono-and bifunctional dihalobenzenes C6H3XHal2 and C6H2XYHal2 (Hal= Br, I; X, Y= F, OR, CF3, CH (OMe) 2) and butyllithium were investigated. The resultant organolithium intermediates were converted into the corresponding benzaldehydes in moderate to good yields. As a rule, bromine atoms in the position ortho to the functional group were replaced preferentially ...