Regioselective halogen-metal exchange reaction of 3-substituted 1, 2-dibromo arenes: The synthesis of 2-substituted 5-bromobenzoic acids

K Menzel, L Dimichele, P Mills, DE Frantz, TD Nelson…

Index: Menzel, Karsten; Dimichele, Lisa; Mills, Paul; Frantz, Doug E.; Nelson, Todd D.; Kress, Michael H. Synlett, 2006 , # 12 p. 1948 - 1952

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Abstract

In general, the regioselective functionalization of the 2-position in 3- or 3,5-substituted bromobenzene derivatives afforded mixtures of 1,3,4- and 1,2,3- or 1,2,3,4- and 1,3,4,5-bromobenzene derivatives, respectively. We envisioned that 3-substituted 1,2-dibromobenzene derivatives could be regioselective functionalized in a halogen-metal exchange reaction. In order to test our hypothesis 1,2-dibromo-3-chlorobenzene (1a) was treated with butyllithium at -78 °C in ...