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Synthesis 1989; 1989(7): 554-556
DOI: 10.1055/s-1989-27317
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A Convenient and Unambiguous Synthesis of 2 (or 7)-Chloronaphthalenes from Substituted α-Tetralones

John D. Prugh* , Albert A. Deana, J. Mark Wiggins
  • *Department of Medicinal Chemistry, Merck Sharp and Dohme Research Laboratories, West Point, PA, 19486, USA
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Publication Date:
12 January 2006 (online)

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2(or 7)-Chlornaphthalenes are unambiguously prepared from α-tetralones(1-oxo-1,2,3,4-tetrahydronaphthalenes) by introducing two chlorines in the 2-position with sulfuryl chloride, reducing the ketone with sodium borohydride, and then converting the resulting hydroxy to chloro with thionyl chloride. Vicinal chlorines are then removed with activated zinc giving a vinyl chloride which is aromatized with 2,3-dichloro-4,5-dicyano-1,4-benzoquinone (DDQ) to give the desired 2(or 7)-chloronaphthalenes.