PROCESS AND INTERMEDIATES FOR THE PREPARATION OF PYROXASULFONE AND FENOXASULFONE

    公开(公告)号:EP4177244A2

    公开(公告)日:2023-05-10

    申请号:EP22198307.5

    申请日:2020-07-10

    申请人: Adama Agan Ltd.

    摘要: 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

    METHODS OF MAKING HALOGENATED PARTIALLY FLUORINATED COMPOUNDS
    7.
    发明公开
    METHODS OF MAKING HALOGENATED PARTIALLY FLUORINATED COMPOUNDS 审中-公开
    卤化部分氟化化合物的制备方法

    公开(公告)号:EP3237367A1

    公开(公告)日:2017-11-01

    申请号:EP15874088.6

    申请日:2015-12-04

    IPC分类号: C07C41/22 C07C41/18 C07C43/12

    摘要: Described herein is method of making a halogenated partially fluorinated compound, comprising: (a) providing a compound having the following structure of formula (I): Rf—CF═CXY wherein X and Y are independently selected from F and Cl; wherein Rf is a fluorinated monovalent group comprising 1 to 10 carbon atoms; (b) contacting the compound with at least one of (i) an iodine or bromine containing salt in the presence of an acid; and (ii) aqueous solution of HZ wherein Z is selected from I and Br to form the halogenated partially fluorinated compound of the formula (II): R′f—CFH—CXYZ wherein X and Y are independently selected from F and Cl; Z is selected from I and Br; and R′f is a fluorinated monovalent group comprising 1 to 10 carbon atoms.

    摘要翻译: 本文描述了制备卤化部分氟化的化合物的方法,其包括:(a)提供具有以下式(I)结构的化合物:其中X和Y独立地选自F和C1; 其中R f是包含1至10个碳原子的氟化一价基团; (b)使所述化合物与(i)在酸存在下的含碘或含溴盐中的至少一种接触; 和(ii)HZ的水溶液,其中Z选自I和Br以形成式(II)的卤化的部分氟化的化合物:其中X和Y独立地选自F和C1; Z选自I和Br; 并且R'f是包含1至10个碳原子的氟化一价基团。