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

Kazuhiko Orito; Takahiro Hatakeyama; Mitsuhiro Takeo; Hiroshi Suginome; Masao Tokuda

doi:10.1055/s-1997-1504

Synthesis 1997; 1997(1): 23-25
DOI: 10.1055/s-1997-1504

short paper

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

Kazuhiko Orito^* , Takahiro Hatakeyama, Mitsuhiro Takeo, Hiroshi Suginome, Masao Tokuda

^*Laboratory of Organic Synthesis, Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060, Japan, Fax +81(11)7066598

Abstract

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A tin(IV) chloride assisted iodo-cyclization of 2-allylphenol gave 2-iodomethyl-2,3-dihydrobenzofuran. A similar cyclization of 2-crotylphenol gave 3-iodo-2-methyl-3,4-dihydro-2H-benzopyran, exclusively. By iodination with mercury(II) oxide-iodine reagent in dichloromethane, 2,3-dihydrobenzofurans or 3,4-dihydro-2H-benzopyrans including the above benzocyclic ethers were easily converted to the corresponding 5- or 6-iodo derivatives, regioselectively, in good yield.

iodination - benzofuran - benzopyran - cyclization - tin(IV) chloride

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