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ChemInform Abstract: Synthesis of 5-Iodobenzofurans and 6-Iodobenzopyrans via Direct Iodination with Mercury(II) Oxide-Iodine Reagent.

✍ Scribed by K. ORITO; T. HATAKEYAMA; M. TAKEO; H. SUGINOME; M. TOKUDA

Publisher: John Wiley and Sons
Year: 2010
Weight: 31 KB
Volume: 28
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199723128

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✦ Synopsis

Synthesis of 5-Iodobenzofurans and 6-Iodobenzopyrans via Direct Iodination with Mercury(II) Oxide-Iodine Reagent.

-5-Iodo-2methylbenzofuran (IV) is synthesized via SnCl4-asisted iodo-cyclization of 2-allylphenol (I) followed by regioselective iodination of (II) and dehydroiodination of (III). Unexpectedly, a similar treatment of 2-crotylphenol (V) gives 3-iodobenzopyran (VI) as the exclusive product. Although chroman-4-one cannot be iodinated under the conditions shown, its iodo derivative (XI) becomes available via the halogenation of the corresponding alcohol (X). -

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