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Brominated and iodinated thiofluoresceins

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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.

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Authors and Affiliations

  1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090, Russia

    V. V. Russkikh, E. V. Vasil’ev & V. V. Shelkovnikov

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  1. V. V. Russkikh
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  2. E. V. Vasil’ev
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  3. V. V. Shelkovnikov
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Correspondence to V. V. Shelkovnikov.

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Original Russian Text © V.V. Russkikh, E.V. Vasil’ev, V.V. Shelkovnikov, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 10, pp. 1559–1563.

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Russkikh, V.V., Vasil’ev, E.V. & Shelkovnikov, V.V. Brominated and iodinated thiofluoresceins. Russ J Org Chem 44, 1538–1542 (2008). https://doi.org/10.1134/S1070428008100242

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  • DOI: https://doi.org/10.1134/S1070428008100242

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