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