Selective fluorination of an aryl triazolinone herbicide intermediate

  • Syvret R
  • Casteel W
  • Lal G
 et al. 
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Abstract

Fluoroaryl 1,2,4-triazolin-5-ones are an important class of herbicidal compounds useful in a variety of crop protection applications, primarily for the control of grassy and broad-leaf plant species. While a number of different synthetic strategies can be used for the step-wise preparation of these complex molecules, it is generally preferred to introduce fluorine later in the synthetic pathway, since the presence of fluorine and other halogens has a dominant effect on all subsequent synthetic steps. We have investigated the reactions that occur between aryl triazolinones and a variety of fluorination agents, including F2/N2, XeF2, (CF3SO2)2NF, Selectfluor®, CF2(OF)2, CF3OF, CH3COOF, and CF3COOF, and have used this knowledge to develop several alternative high-yielding routes to fluoroaryl 1,2,4-triazolin-5-ones. The fluorine introduction strategy and experimental results for a representative example of this important class of compounds are discussed herein. © 2003 Elsevier B.V. All rights reserved.

Author-supplied keywords

  • Direct fluorination
  • Electrophilic fluorination
  • Fluorination of aryl triazolinone
  • Fluoroaryl triazolinone
  • Selective fluorination

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Authors

  • Robert G. Syvret

  • William J. Casteel

  • G. Sankar Lal

  • Jaidev S. Goudar

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