Journal of Organic Chemistry 2007-12-07

Halogen-metal exchange in 1,2-dibromobenzene and the possible intermediacy of 1,2-dilithiobenzene.

Holger F Bettinger, Matthias Filthaus

Index: J. Org. Chem. 72(25) , 9750-2, (2007)

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Abstract

The one-step high-yield synthesis of 1,2-bis(trimethylsilyl)benzene from 1,2-dibromobenzene using tert-butyllithium and trimethylsilyltriflate is reported. A mechanistic investigation shows that 1,2-dilithiobenzene is not an intermediate in this reaction; the coexistence of trimethylsilyltriflate and tert-butyllithium at very low temperatures allows a sequence of bromine-lithium exchange and subsequent derivatization reactions to operate.