The Journal of organic chemistry

ortho-Metalation of Unprotected 3-bromo and 3-chlorobenzoic acids with hindered lithium dialkylamides

F Gohier, J Mortier

文献索引：Gohier, Frederic; Mortier, Jacques Journal of Organic Chemistry, 2003 , vol. 68, # 5 p. 2030 - 2033

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被引用次数: 48

摘要

Upon treatment of 3-chloro/bromobenzoic acids with hindered lithium dialkylamides (LDA or LTMP) at-50° C, lithium 3-chloro/bromo-2-lithiobenzoates are generated. These dianions can be trapped as such to afford after electrophilic quenching a variety of simple 2- substituted-3-chloro/bromobenzoic acids. The 3-bromo-2-lithiobenzoate is less stable than the corresponding 3-chloro derivative and partly eliminates lithium bromide, thus setting ...