- In situ Generation of Hypervalent Iodine Reagents for the Electrophilic Chlorination of Arenes
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Efficient metal-free methods for the electrophilic chlorination of arenes using PIFA and simple chlorine sources are reported. The in situ formation of PhI(Cl)OCOCF3 from PIFA and KCl is proposed, which resulted in a chlorinating species for moderately activated arenes. Moreover, the in situ formation of PhICl2 from PIFA and TMSCl resulted in an excellent approach for the chlorination of a great variety of arenes (20 examples) in high yields, even when working on a multigram scale.
- Granados, Albert,Jia, Zhiyu,del Olmo, Marc,Vallribera, Adelina
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p. 2812 - 2818
(2019/04/08)
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- Story of an Age-Old Reagent: An Electrophilic Chlorination of Arenes and Heterocycles by 1-Chloro-1,2-benziodoxol-3-one
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By the use of 1-chloro-1,2-benziodoxol-3-one, an age-old reagent, the practical and efficient chlorination method is achieved. This hypervalent iodine reagent is amenable not only to the chlorination of nitrogen-containing heterocycles but also to selected classes of arenes, BODIPY dyes, and pharmaceuticals. In addition, the advantages, such as easy preparation and recyclable, air- and moisture-stable, in combination with the success in a gram-scale experiment grant this reagent great potential for industrial application.
- Wang, Mengzhou,Zhang, Yanyan,Wang, Tao,Wang, Chao,Xue, Dong,Xiao, Jianliang
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supporting information
p. 1976 - 1979
(2016/06/01)
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- PROCESS FOR SYNTHESIS FIPRONIL
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The present disclosure relates to a process for trifluoromethylsulfinyl pyrazole compound of formula I, from a compound of formula III, wherein, R, R1 and R2 represent a group containing halogen group respectively and R3 represents a perhaloalkyl.
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Paragraph 0060
(2013/03/26)
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- PROCESS FOR SYNTHESIS OF FIPRONIL
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A process for preparation of a trifluoromethylsulfinyl pyrazole compound of formula (I) from a compound of formula (III) is provided, wherein R, R1 and R2 represent a group containing halogen respectively and R3 represents a perhaloalkyl.
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Page/Page column 17
(2011/10/03)
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- PROCESS FOR PREPARING POLYHALOGENATED PERHALOALKYLANILINE
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A method for preparing polyhalogenated p-trifluoromethylanilines, especially 2,6-dihalo-p-trifluoromethylaniline is provided The method comprises reacting ammonia with 3,4-dihalobenzotrifluoride at a temperature ranging from 200 °C to 300 °C in the presence of an alkali halide, and then halogenating the resultant intermediates with halogenating agents like sulfuryl chloride, chlorine and PC15 to get 2,6-dihalo-p-trifluoromethylaniline.
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Page/Page column 12
(2011/06/16)
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- Trifluoromethylation of various aromatic compounds by CF3I in the presence of Fe(II) compound, H2O2 and dimethylsulfoxide
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Trifluoromethylation of aromatic and hetero-aromatic compounds by CF3I in the presence of Fe(II) compound, H2O2 and dimethylsulfoxide was investigated. Various trifluoromethylated benzene derivatives, six-membered nitrogen-containing aromatic compounds and five-membered hetero-aromatic compounds were obtained under mild conditions. General orientation of electrophilic substitution of aromatic compounds was observed similarly as reported in other radical trifluoromethylation previously.
- Kino, Tatsuhito,Nagase, Yu,Ohtsuka, Yuhki,Yamamoto, Kyoko,Uraguchi, Daisuke,Tokuhisa, Kenji,Yamakawa, Tetsu
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experimental part
p. 98 - 105
(2010/03/03)
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- NOVEL PROCESS FOR THE PREPARATION OF A SYNTHETIC INTERMEDIATE FOR PESTICIDES
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Process for the preparation of a compound of general formula (I): in which X represents a halogen atom, by reaction of para-trifluoromethylaniline of formula (II): with a dihalogen x2, the two compounds being introduced simultaneously into a polar aprotic solvent in a dihalogen/compound (II) molar ratio ranging from 1.9 to 2.5 and at a temperature ranging from 100 to 300° C.
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- Processes for preparing pesticidal intermediates
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Compounds of formula (I) are prepared by hydrogenolysis of a compound of formula (II): where R1is haloalkyl, haloalkoxy or ?SF5; W is N or CR3; and R2and R3are H or Cl. The compounds of formula (I) can be used as intermediates in the preparation of pesticidally active arylpyrazole compounds.
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Page column 6
(2008/06/13)
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- Process for preparing trifluoromethylanilines
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A process for preparing trifluoromethylanilines of the formula (I), STR1 in which R1 and R2, independently of each other, are hydrogen, halogen, (C1 -C4) alkyl, hydroxyl, alkoxy, alkylthio, carboxyl, or a nitro or cyano group, by reacting compounds of the formula (II) STR2 in which X1, X2 and X3 are in each case, identically or differently, halogen atoms, a is 0 or 1, Y is fluorine, chlorine or bromine, and R1 and R2 have the defined meaning, with anhydrous hydrofluoric acid, and converting the resulting aniline hydrofluorides with a base into the free amines.
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- Reactions of Trifluoromethyl Bromide and Related Halides: Part 10. Perfluoroalkylation of Aromatic Compounds induced by Sulphur Dioxide Radical Anion Precursors
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Perfluoroalkylation of electron-rich aromatic compounds with trifluoromethyl bromide, or long-chain perfluoroalkyl iodides, was performed in the presence of sodium dithionite or zinc-sulphur dioxide.This alkylation occurred at the ortho and para positions relative to the amino or hydroxy substitutent.Pyrroles were perfluoroalkylated regioselectively at the 2-position.This alkylation was interpreted as a radical aromatic substitution; the formation of the perfluoroalkyl radical can be induced by a single-electron transfer from sulphur dioxide radical anion to the perfluoroalkyl halide.
- Tordeux, Marc,Langlois, Bernard,Wakselman, Claude
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p. 2293 - 2299
(2007/10/02)
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- Perfluoroalkylation of Anilines in the Presence of Zinc and Sulphur Dioxide
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Arylamines are transformed into their ortho- and para-trifluoromethyl derivatives by the action of trifluoromethyl bromide under slight pressure in the presence of 0.15 equiv. of zinc and sulphur dioxide in dimethylformamide.
- Wakselman, Claude,Tordeux, Marc
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p. 1701 - 1703
(2007/10/02)
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