http://rdf.ncbi.nlm.nih.gov/pubchem/patent/WO-2022009044-A1

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filingDate 2021-07-02-04:00^^<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 2022-01-13-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber WO-2022009044-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), wherein Y = protecting group. 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. Ar = 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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