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Synthesis 1987; 1987(1): 35-37
DOI: 10.1055/s-1987-27832
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A New Method for the Synthesis of tert-Alkyl Chlorides from tert-Alcohols

David Crich* , Simon M. Fortt
  • *Department of Chemistry, University College London, 20 Gordon Street, London, WC1H OAJ, UK
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Publication Date:
20 August 2002 (online)

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Tert-Alkyl chlorides 5 are prepared in good yield from the corresponding alcohols 1 in a facile two step synthesis. The method involves treatment of the corresponding crude oxalyl monochloride alkyl ester 2 with N-hydroxy-pyridine-2-thione sodium salt 3 in tetrachloromethane at reflux to give the bright yellow N-(alkoxyoxalyloxy) pyridine-2-thiones 4 which undergo decomposition to the chlorides 5 in good yield. The reaction is conveniently monitored by the loss of colour from the mixed anhydride.

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