The Journal of Organic Chemistry

Selective halogen-lithium exchange in 2, 5-dibromobenzenes and 2, 5-dibromopyridine

WE Parham, RM Piccirilli

Index: Parham,W.E.; Piccirilli,R.M. Journal of Organic Chemistry, 1977 , vol. 42, # 2 p. 257 - 260

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Citation Number: 136

Abstract

Reaction of a series of 2, 5-dibromo-substituted aromatic systems with 1 equiv of n- butyllithium at-100" C results in high selectivity of halogen-metal exchange when the substituent contains unshared electrons. The results suggest that product distribution at-100" C is determined by thermodynamic rather than kinetic factors. Fair to excellent yields of derivatives of the monolithium intermediates have been obtained. Reaction of 2, 5- ...