Synthesis and Characterization of 2,7-Dibromo-N-octylcarbazole
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TQ612.6

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    Abstract:

    2,7-Dibromo-N-octylcarbazole (3) was synthesized from 4,4,-dibromobiphenyl by nitration, the Cadogan cyclization and N-alkylation. Nitration of 4,4,-dibromobiphenyl by HNO3 with n(4,4,-dibromobiphenyl)︰n(HNO3)=1.0︰4.0 gave 4,4,-dibromo-2-nitrobiphenyl (1) with a yield of 97% at 75 ℃ for 5 h. The cyclization of 1 by triphenylphosphine with n(4,4,-dibromo-2- nitrobiphenyl) : n(triphenylphosphine)=1.0 : 3.0 gave 2,7-dibromocarbazole (2) with a yield of 68% in Schlenk flask. N-alkylation of 2 by bromooctane with n(2,7-dibromocarbazole) : n(bromooctane)=1.0 : 1.5 gave the title product with a yield of 85% under the alkaline conditions. The structure of the product was characterized by IR, elementary analysis and 1H NMR spectra.

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History
  • Received:March 26,2012
  • Revised:May 15,2012
  • Adopted:May 15,2012
  • Online: August 20,2012
  • Published:
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