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Synthesis 1988; 1988(12): 950-952
DOI: 10.1055/s-1988-27762
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The Synthesis of 5-Substituted 2,3-Dihydrobenzofurans

Ramon J. Alabaster* , Ian F. Cottrell, Hugh Marley, Stanley H. B. Wright
  • *Development Laboratories, Merck Sharp and Dohme Research Laboratories, Hertford Road, Hoddesdon, Hertfordshire, EN11, 9BU, England
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Publication Date:
20 August 2002 (online)

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The preparation of 2,3-dihydrobenzofurans 6 from 2-(2-bromophenoxy)ethyl chlorides 3 by reaction with magnesium in a development of the Parham cyclialkylation reaction is described. A high yielding procedure using phase-transfer catalysis has also been developed for the preparation of the intermediate chloroethyl ethers 3 from bromophenols 2. The 5-hydroxy derivative 15 may be obtained from 2,3 dihydrobenzofuran (6a) by reaction with electrophilic reagents followed by oxidation.