13656-49-0Relevant articles and documents
A 2, 4 - difluoro - 3, 5 - dichloro nitrobenzene synthesis of 1, 3, 5 - trichloro - 2, 4, 6 - trifluorobenzene
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Paragraph 0052; 0053; 0054; 0055; 0056; 0057, (2017/08/25)
The invention discloses a method for synthesizing 1,3,5-trichloro-2,4,6-trifluorobenzene from 2,4-difluoro-3,5-dichloronitrobenzene. The method comprises performing chlorination reaction on 2,4-difluoro-3,5-dichloronitrobenzene in chlorine atmosphere to obtain a chloride, and controlling the chlorination reaction temperature to 160-195 DEG C; performing nitration reaction on the chloride in a mixed acid solution of sulfuric acid and nitric acid to obtain a nitro compound, and controlling the nitration reaction temperature to 60-110 DEG C; and performing fluorination reaction on the nitro compound with a fluoride under a waterless condition so as to obtain 1,3,5-trichloro-2,4,6-trifluorobenzene, and controlling the fluorination reaction temperature to 80-200 DEG C. The product synthesized by the method is high in selectivity, and the yield and the purity of products of all steps are relatively high, and operation is simple.
Fluorinated biphenyls from aromatic arylations with pentafluorobenzenediazonium and related cations. Competition between arylation and azo coupling
Kosynkin, Dmitry,Bockman, T. Michael,Kochi, Jay K.
, p. 2003 - 2012 (2007/10/03)
High yields of the mixed perfluorinated biaryls (C6F5-Ar) are obtained by the catalytic dediazonlatlon of the pentafluorobenzenediazonium salt (C6F5N2+BF4-) in acetonitrile solutions containing various aromatic substrates (ArH) together with small amounts of iodide salts. Activated (electron-rich) as well as deactivated (electron-poor) arenes are successfully pentafluorophenylated by this method. The arylation is distinct from the azo coupling of the same substrates, which takes place in the absence of the iodide catalyst and yields the corresponding diazene (C6F5N=N-Ar) as product. The catalytic role of iodide, and the isomeric product distributions obtained with this procedure indicate that the arylation proceeds via the pentafluorophenyl radical in a efficient homolytic chain process. Since azo coupling involves electrophilic aromatic substitution of electron-rich ArH by C6F5N2+, the two competing pathways are distinct and do not have reactive intermediates in common.