Synthesis of 1-bromo-6-cyano-2-naphthol
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O621.3;O621.3

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    Abstract:

    6-Bromo-2-naphthol (4) was prepared from 2-naphthol (2) via a two-step one-pot process in a yield of 89.0%; then 6-cyano-2-naphthol (5) was synthesized from 4 under the feeding ratio of n(CuCN):n(4)=1.5:1 in a yield of 91.2%. In the end, the bromination reagents Br2 and NBS were both adopted to prepare 1-bromo-6-cyano-2-naphthol (1) from 5. In the case of Br2 as bromination reagent, acetic acid as solvent, n(Br2):n(5) = 1:1, the yield is 89.8%;and this process is low-cost and suitable for industrialization. In the case of NBS as bromination reagent, acetonitrile as solvent, n(NBS):n(5)=1.00:1.03, the yield is 99.2%; this method is mild, simple, efficient for laboratory-scale preparation in which the problems of volatilization and high inhalation toxicity of Br2 are avoided.

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History
  • Received:August 10,2013
  • Revised:September 02,2013
  • Adopted:September 17,2013
  • Online: January 03,2014
  • Published:
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