- Construction of Sulfonyl Phthalides via Copper-Catalyzed Oxysulfonylation of 2-Vinylbenzoic Acids with Sodium Sulfinates
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Copper-catalyzed difunctionalization of 2-vinylbenzoic acids with sodium sulfinates to construct substituted lactones has been realized. This protocol employs inexpensive CuCl2 as the catalyst, di-tert-butyl peroxide or O2 as the terminal oxidant, and readily available sodium sulfinates as sulfonylation reagents. High functional group tolerance and excellent yields were demonstrated by the efficient preparation of a wide range of γ-sulfonylated phthalides.
- Xiong, Yan-Shi,Zhang, Bin,Yu, Yang,Weng, Jiang,Lu, Gui
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p. 13465 - 13472
(2019/10/16)
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- PROCESS FOR THE PREPARATION OF FIPRONIL AND ANALOGUES THEREOF
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The present invention relates to a new and efficient process for preparing 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(trifluoromethylthio)-IH-pyrazole-3-carbonitrile (hereinafter referred to as compound of formula I), which is useful as an intermediate for the antiparasitic agent fipronil, and a process for preparing 5-amino-3-cyano-l-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethyl sulfinylpyrazole (hereinafter referred to as compound of formula II or fipronil). In one aspect, there is provided a process for preparing fipronil comprising: a) a step of reacting CF3S(=O)ONa with the compound of formula (III) in the presence of a reducing/halogenating agent; and b) a step of oxidizing the compound of formula (I) obtained in step a) in the presence of a selective oxidizing agent, under suitable conditions, wherein the selective oxidizing agent selectively effects oxidation of (I) to the corresponding sulfoxide, Fipronil. In certain exemplary embodiments, the selective oxidizing agent is MHSO5, wherein M is an alkaline metal cation.
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Page/Page column 27-28
(2009/07/18)
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- A new preparation of trifluoromethanesulfinate salts
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Trifluoromethanesulfinate (triflinate) salts can be prepared in an ecofriendly way by β-elimination of aliphatic triflones bearing an acidic hydrogen in β position. This technique allows the synthesis of various triflinate salts under mild conditions.
- Langlois, Bernard R.,Billard, Thierry,Mulatier, Jean-Christophe,Yezeguelian, Catherine
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p. 851 - 856
(2008/03/13)
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- Practical and efficient synthesis of perfluoroalkyl iodides from perfluoroalkyl chlorides via modified sulfinatodehalogenation
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A novel two-step one pot synthesis of perfluoroalkyl iodides (α,ω-diiodoperfluoroalkanes) from perfluoroalkyl chlorides (α-chloro-ω-iodoperfluoroalkanes) has been developed by initial conversion to the corresponding sodium perfluoroalkanesulfinates with sodium dithionite and then subsequent oxidation by iodine.
- Cao, Hai-Ping,Chen, Qing-Yun
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p. 1187 - 1190
(2008/02/10)
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- Process for producing perfluoroalkanesulfinate
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The invention relates to a process for producing an alkali metal salt of a perfluoroalkanesulfinic acid. This process includes the step of bringing a perfluoroalkanesulfonic fluoride into contact with an alkali metal salt of sulfurous acid in the presence of water. This process is useful, since this perfluoroalkanesulfonic fluoride (e.g., trifluoromethanesulfonic fluoride) is easily available.
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- ELECTROCHEMICAL SYNTHESIS OF TRIFLUOROMETHANE SULFINIC ACID SALT FROM CF3Br AND SO2
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The electroreduction of a mixture of SO2 and CF3Br in DMF, in an undivided cell with a soluble anode (Mg or Zn) lead to salt of trifluoromethane sulfinic acid in high yield.
- Folest, Jean-Claude,Nedelec, Jean-Yves,Perichon, Jacques
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p. 1491 - 1494
(2007/10/02)
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- Triflic acid: synthesis from bromotrifluoromethane
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A chemical method for the preparation of trifluoromethanesulfonic acid is described.A metal selected from zinc, aluminium, manganese and cadmium is mixed with dimethylformamide and sulfur dioxide.Then, trifluoromethyl bromide is introduced under pressure in this mixture.The trifluoromethyl sulfinate is isolated as sodium salt.Oxidation by hydrogen peroxide followed by hydrolysis leads to trifluoromethanesulfonic acid.
- Wakselman, Claude,Tordeux, Marc
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p. 868 - 870
(2007/10/02)
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- Trifluormethansulfinsaeure-Azid und Trifluormethan-Schwefeloxidnitrid - Synthese und chemische Eigenschaften
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The synthesis of a perfluoroalkyl derivative of sulfanuric acid was attempted via the thermal decomposition of a) F3CSO2NPCl3 to yield OPCl3 as a byproduct, b) F3CSON3 to give the desired product by splitting off elemental nitrogen.However F3CSO2NPCl3 unexpectedly is stable up to 500 deg, when it looses mainly the F3C-group.Trifluoromethane sulfinic acidazide, F3CSON3, which we synthesised from the acid chloride and NaN3 at -40 deg starts to decompose as expected around -10 deg forming as the primary intermediate F3CSON, which can be formulated containing a S-N triple bond, and which proved to be extremely reactive.This trifluoromethan-sulfur oxide nitride oligomerizes spontaneously, or in presence of suitable compounds can be captured to yield various new compounds.With acetonitril a dithiatriazin is formed, with F3CSON3 an explosive sulfonimidoyl-azide, with trimethylsilyl azide, N-trimethylsilyl-trifluoromethan-sulfonimidoyl chloride.F3CSOCl yields an N-substituted sulfonimidoyl chloride in two diastereomeric forms.
- Bechtold, Thomas,Eingelbrecht, Alfred
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p. 379 - 402
(2007/10/02)
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