Catalytic nucleophilic fluorination by an imidazolium ionic liquid possessing trialkylphosphine oxide functionality

  • Paramanik M
  • Singh R
  • Mukhopadhyay S
 et al. 
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Abstract

Abstract The synthesis of a new alkylmethylimidazolium ionic liquid wherein the alkyl group is functionalized with dihexylphosphine oxide moiety at the terminal position has been achieved in four steps from 1-methylimidazole. This hybrid ionic liquid effectively catalyzed the nucleophilic fluorination of primary alkyl mesylates under mild conditions using CsF as the fluoride source with a faster rate compared to butylmethylimidazolium mesylate. The hybrid catalyst was recycled 5 times without compromising the yield and purity of the product. The nucleophilic fluorination has been used for the synthesis of diethyl 2-(5-fluoropentyl)-2-methyl malonate, a precursor of 18F isotopomer of an apoptosis imaging agent and the protected form of O-(2'-fluoroethyl)-l-tyrosine, a 18F isotopomer of a tumor imaging agent.

Author-supplied keywords

  • Alkyl mesylates
  • Catalysis
  • Fluorination
  • Ionic liquid
  • Nucleophilic substitution

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Authors

  • Minakshmi Paramanik

  • Rekha Singh

  • Sulekha Mukhopadhyay

  • Sunil K. Ghosh

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