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

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Journal of Industrial Microbiology & Biotechnology

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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Acknowledgments

We thank Dr. M. Futran for his support during the internship period of Mr. Hamish Christie. We also thank R. Hanson, B. Davis, and D. Brzozowski for their microbiological support.

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Author notes

  1. Hamish Christie

    Present address: Department of Chemistry, Venable & Kenan Laboratories, The University of North Carolina at Chapel Hill, Box 3290, Chapel Hill, NC, 27599-3290, USA

Authors and Affiliations

  1. Department of Process Research and Development, Bristol-Myers Squibb Pharmaceutical Research Institute, 1 Squibb Dr, New Brunswick, NJ, 08903, USA

    Prashant P. Deshpande, Venkata B. Nanduri, Annie Pullockaran, Hamish Christie, Richard H. Mueller & Ramesh N. Patel

Authors
  1. Prashant P. Deshpande
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  2. Venkata B. Nanduri
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  3. Annie Pullockaran
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  4. Hamish Christie
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  5. Richard H. Mueller
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  6. Ramesh N. Patel
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Correspondence to Prashant P. Deshpande or Ramesh N. Patel.

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Deshpande, P.P., Nanduri, V.B., Pullockaran, A. et al. Microbial hydroxylation of o-bromophenylacetic acid: synthesis of 4-substituted-2,3-dihydrobenzofurans. J Ind Microbiol Biotechnol 35, 901–906 (2008). https://doi.org/10.1007/s10295-008-0363-4

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  • DOI: https://doi.org/10.1007/s10295-008-0363-4

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