title: Microbial hydroxylation of o-bromophenylacetic acid: synthesis of 4-substituted-2,3-dihydrobenzofurans.
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.
authors.affiliation: Department of Process Research and Development, Bristol-Myers Squibb Pharmaceutical Research Institute, New Brunswick, NJ 08903, USA. prashant.deshpande@bms.com.
authors.forename: Prashant P
authors.initials: PP
authors.lastname: Deshpande
authors.forename: Venkata B
authors.initials: VB
authors.lastname: Nanduri
authors.forename: Annie
authors.initials: A
authors.lastname: Pullockaran
authors.forename: Hamish
authors.initials: H
authors.lastname: Christie
authors.forename: Richard H
authors.initials: RH
authors.lastname: Mueller
authors.forename: Ramesh N
authors.initials: RN
authors.lastname: Patel
mesh_terms: D001230:Aspergillus / Q000378:metabolism*; D001572:Benzofurans / Q000378:metabolism*; D001711:Biotransformation; D006900:Hydroxylation; D015394:Molecular Structure; D010648:Phenylacetates / Q000378:metabolism*
chemical_list: D001572:Benzofurans; D010648:Phenylacetates; C043168:coumaran; C025136:phenylacetic acid