A practical method for stabilizing lithiated halogenated aromatic compounds

T Rawalpally, Y Ji, A Shankar, W Edwards…

Index: Rawalpally, Thimma; Ji, Yaohui; Shankar, Ashish; Edwards, William; Allen, Joshua; Jiang, Yong; Cleary, Thomas P.; Pierce, Michael E. Organic Process Research and Development, 2008 , vol. 12, # 6 p. 1293 - 1298

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Citation Number: 12

Abstract

An exothermic decomposition was observed during a metalation/acylation of 3, 4- difluoroanisole (5), resulting in a significant thermal hazard. The lithiated anion 6 was found to decompose exothermically at temperatures above− 47° C showing an adiabatic temperature rise at a peak rate of 120° C/min. A literature search revealed similar observations for metalation/acylation in analogous aromatic difluoro compounds. This ...