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filingDate 2020-07-10-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_421b1088a50836f19e99f8df2567bdb4
http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_03b79bf597542ad6a073943d5e5615d8
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publicationDate 2022-01-12-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber EP-3936503-A1
titleOfInvention Process and intermediates for the preparation of pyroxasulfone, fenoxasulfone and various sulfone analogs of 5,5-dimethyl-4h-1,2-oxazole
abstract The invention relates to a process for preparing immediate precursors for pyroxasulfone and fenoxasulfone preparation of the formula (I). The process comprises a bromination reaction of a benzylic position without light irradiation (step a ), followed by thoination reaction, which substitutes the bromine atom (step b ) and after the protecting group is removed, and the revealed thiol or thiolate reacts with a substituted isoxazoline bearing a leaving group at the 3-position (step c ).n nwherein nY = protecting group n In another variant of the invention the pyroxasulfone or fenoxasulfone immediate precursor is synthesized from the arylmethyl bromide by first forming a carbon-sulfur bond at the 3-position of a 2-isoxazoline through displacement of a leaving group at the 3-position (particularly acid derived residues such as phosphoryl, sulfanyl, halo, cyano or carboxyl groups) by an appropriate thionating reagent. The resulting adducts, which is a S-protected 3-thio-2-isoxazoline, may be treated with base to remove the protecting group, to reveal a thiol or thiolate which may subsequently react with the arylmethyl bromide to form the Pyroxasulfone or Fenoxasulfone immediate precursor.n nAr = aryl, Y = protecting group and X = leaving group
priorityDate 2020-07-10-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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