Russian Journal of Organic Chemistry

, Volume 44, Issue 10, pp 1538–1542 | Cite as

Brominated and iodinated thiofluoresceins

  • V. V. Russkikh
  • E. V. Vasil’ev
  • V. V. Shelkovnikov
Article

Abstract

Conditions were found for the synthesis of mono-, di-, tri-, and tetrabromo- and -iodo-substituted thiofluoresceins. Iodination and bromination of thiofluorescein with molecular iodine and bromine in 1 N aqueous sodium hydroxide gave mixtures of the corresponding 2,4,5,7-tetra- and 2,4,5-trihalo derivatives in 71/14 (Y = I) and 73/13% yield (Y = Br), respectively. In the reactions of thiofluorescein with bromine in acetic acid and with iodine in methanol at a substrate-to-halogen ratio of 1 : 2, 4,5-dibromo- and 4,5-diiodothiofluoresceins were isolated in 56 and 67% yield. Analogous reactions with equimolar amounts of the reactants produced 59% of 4-bromothiofluorescein and 51% of 4-iodothiofluorescein.

Keywords

Electronic Absorption Spectrum Aqueous Sodium Hydroxide Molecular Iodine Lactone Form Thioxanthen 

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Copyright information

© MAIK Nauka 2008

Authors and Affiliations

  • V. V. Russkikh
    • 1
  • E. V. Vasil’ev
    • 1
  • V. V. Shelkovnikov
    • 1
  1. 1.Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian DivisionRussian Academy of SciencesNovosibirskRussia

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