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Synthesis 1989; 1989(8): 598-603
DOI: 10.1055/s-1989-27329
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Synthesis of 6-(3-Aryl-2-propenyl)-2,3-dihydro-5-hydroxybenzofuran Derivatives by Cross Coupling Reactions

Ramon J. Alabaster* , Ian F. Cottrell, David Hands, Guy R. Humphrey, Derek J. Kennedy, Stanley H. B. Wright
  • *Merck Sharp and Dohme Research Laboratories, Hertford Road, Hoddesdon, Hertfordshire, EN11 9BU, England
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Publication History

Publication Date:
17 September 2002 (online)

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The synthesis of 6-(3-aryl-2-propenyl)-2,3-dihydro-5-hydroxybenzofuran derivatives by cross coupling between 6-bromo-2,3-dihydro-benzofurans and cinnamyl halides via organo-metallic compounds has been explored. Palladium catalysed reaction between benzofurylzinc bromides and cinnamyl acetates gave high yields of pure products, and the reaction was developed into an economic process for the large scale preparation of 2,3-dihydro-5-hydroxy-6-[3-(2-hydroxymethylphenyl)-2-propenyl]benzofuran, a topical anti-inflammatory agent.