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      Permanent link:
      https://www.ias.ac.in/article/fulltext/jcsc/124/05/1077-1085

    • Keywords

       

      Fries rearrangement; selective 𝛼-bromination; cyclisation; Friedel-Crafts acylation.

    • Abstract

       

      A practical synthesis of (2-butyl-5-nitrobenzofuran-3-yl)(4-hydroxyphenyl)methanone, a key intermediate in the preparation of anti arrhythmic drug, is described. The commercially available 4-nitrophenol (3) is converted in five steps to 2-butyl-5-nitrobenzofuran (9) which upon Friedel-Crafts acylation with 4-methoxybenzoyl chloride followed by deprotection of methyl group gives (2).

    • Author Affiliations

       

      P Raja Gopal1 2 E R R Chandrashekar1 M Saravanan1 B Vijaya Bhaskar1 P Veera Somaiah2

      1. Research and Development, Dr. Reddy’s Laboratories Ltd., Integrated Product Development Organization, Hyderabad 500 072, India
      2. Department of Chemistry, Osmania University, Hyderabad 500 007, India

    • Dates

       
      Published
      September 2012
      Manuscript received
      30 September 2011
      Manuscript revised
      13 March 2012
      Accepted
      19 April 2012

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