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Synlett 1991; 1991(9): 631-632
DOI: 10.1055/s-1991-20821
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(Bromomethyl) lithium: Efficient in situ Reactions

T. John Michnick* , Donald S. Matteson
  • *Department of Chemistry, Washington State University, Pullman, Washington 99164-4630, USA
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Publication Date:
07 March 2002 (online)

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(Bromomethyl)lithium has been generated by the addition of butyllithium to dibromomethane in the presence of suitable substrates in tetrahydrofuran at -78 °C. Aldehydes or ketones yielded oxiranes (85-93%), triisopropyl borate yielded diisopropyl (bromomethyl)boronate (89%), and boronic esters without functional substituents underwent methylene insertion into the carbon-boron bond (95-97%).

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