An Improved Process for the Preparation of an ?,?-Difluorosulfonylisoxazoline Herbicide

Authors

  • Chantal Belie Syngenta Crop Protection, Jealott's Hill International Research Centre, Bracknell, Berkshire RG42 6EY, UK
  • Andrew Plant Syngenta Crop Protection AG, CH-4002 Basel, Switzerland
  • Nick Mulholland Syngenta Crop Protection, Jealott's Hill International Research Centre, Bracknell, Berkshire RG42 6EY, UK
  • Matthew McLachlan Syngenta Crop Protection, Jealott's Hill International Research Centre, Bracknell, Berkshire RG42 6EY, UK
  • Derek McCormack Syngenta Crop Protection, Jealott's Hill International Research Centre, Bracknell, Berkshire RG42 6EY, UK
  • Adrian Longstaff Syngenta Crop Protection, Jealott's Hill International Research Centre, Bracknell, Berkshire RG42 6EY, UK
  • Tony Kozakiewicz Syngenta Crop Protection, Jealott's Hill International Research Centre, Bracknell, Berkshire RG42 6EY, UK
  • Andy Knee Syngenta Crop Protection, Jealott's Hill International Research Centre, Bracknell, Berkshire RG42 6EY, UK
  • Katharine Ingram Syngenta Crop Protection, Jealott's Hill International Research Centre, Bracknell, Berkshire RG42 6EY, UK
  • Myriem El Qacemi Syngenta Crop Protection Münchwilen AG, Schaffhauserstrasse, CH-4332 Stein, Switzerland. myriem.el_qacemi@syngenta.com
  • Martin Diggelmann Syngenta Crop Protection AG, CH-4002 Basel, Switzerland
  • Jonathan Dallimore Syngenta Crop Protection, Jealott's Hill International Research Centre, Bracknell, Berkshire RG42 6EY, UK
  • Anne Dalençon Syngenta Crop Protection, Jealott's Hill International Research Centre, Bracknell, Berkshire RG42 6EY, UK
  • Eric Clarke Syngenta Crop Protection, Jealott's Hill International Research Centre, Bracknell, Berkshire RG42 6EY, UK
  • Jutta Boehmer Syngenta Crop Protection, Jealott's Hill International Research Centre, Bracknell, Berkshire RG42 6EY, UK
  • John Williams Syngenta Crop Protection, Jealott's Hill International Research Centre, Bracknell, Berkshire RG42 6EY, UK

DOI:

https://doi.org/10.2533/chimia.2014.442

Keywords:

Defluorinative silylation, Herbicide, Process chemistry

Abstract

An efficient synthesis of a difluorosulfone-containing herbicide has been achieved by selective reductive silylation of a symmetrical bis(trifluoromethyl)-1,2,3-triazole. Subsequently, a fluoride-induced reaction led to a difluoromethyl anion equivalent, which was reacted with a sulfur electrophile leading ultimately to the key difluorosulfide moiety.

Downloads

Published

2014-06-26

Issue

Section

Scientific Articles