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Ethylenebis(N-methylimidazolium) ditribromide (EBMIDTB): an efficient reagent for the monobromination of 1,3-diketones and β-ketoesters

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Abstract

Ethylenebis(N-methylimidazolium) ditribromide, a stable crystalline solid, is easily prepared by reaction of the corresponding dibromide salt with bromine in n-hexane. 1,3-Diketones and β-ketoesters can be brominated chemoselectively to the corresponding α-monobrominated products by using this reagent at 0–5 °C. Under the same reaction conditions, diethyl malonate, ethyl cyanoacetate, and malonitrile were monobrominated at moderate yield.

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Acknowledgment

We are thankful to the Research Council of Mazandaran University for the partial support of this work.

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemistry, Mazandaran University, Babolsar, Iran

    Rahman Hosseinzadeh, Mahmood Tajbakhsh & Zahra Lasemi

  2. Department of Biology, Faculty of Science, Mazandaran University, Babolsar, Iran

    Maryam Mohadjerani

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  1. Rahman Hosseinzadeh
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  2. Mahmood Tajbakhsh
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  3. Maryam Mohadjerani
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  4. Zahra Lasemi
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Correspondence to Rahman Hosseinzadeh.

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Hosseinzadeh, R., Tajbakhsh, M., Mohadjerani, M. et al. Ethylenebis(N-methylimidazolium) ditribromide (EBMIDTB): an efficient reagent for the monobromination of 1,3-diketones and β-ketoesters. Monatsh Chem 140, 57–60 (2009). https://doi.org/10.1007/s00706-008-0020-7

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  • DOI: https://doi.org/10.1007/s00706-008-0020-7

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