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Microbial hydroxylation of o-bromophenylacetic acid: synthesis of 4-substituted-2,3-dihydrobenzofurans

Authors
  • Deshpande, Prashant P.1
  • Nanduri, Venkata B.1
  • Pullockaran, Annie1
  • Christie, Hamish1, 2
  • Mueller, Richard H.1
  • Patel, Ramesh N.1
  • 1 Bristol-Myers Squibb Pharmaceutical Research Institute, Department of Process Research and Development, 1 Squibb Dr, New Brunswick, NJ, 08903, USA , New Brunswick (United States)
  • 2 The University of North Carolina at Chapel Hill, Department of Chemistry, Venable & Kenan Laboratories, Chapel Hill, NC, 27599-3290, USA , Chapel Hill (United States)
Type
Published Article
Journal
Journal of Industrial Microbiology & Biotechnology
Publisher
Springer-Verlag
Publication Date
May 22, 2008
Volume
35
Issue
8
Pages
901–906
Identifiers
DOI: 10.1007/s10295-008-0363-4
Source
Springer Nature
Keywords
License
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Abstract

Microbial hydroxylation of o-bromophenylacetic acid provided 2-bromo-5-hydroxyphenylacetic acid. This enabled a route to the key intermediate 4-bromo-2,3-dihydrobenzofuran for synthesizing a melatonin receptor agonist and sodium hydrogen exchange compounds. Pd-mediated coupling reactions of 4-bromo-2,3-dihydrobenzofuran provided easy access to the 4-substituted-2,3-dihydrobenzofurans.

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