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Polyhalogenonitrobenzenes and derived compounds Part 5. Improved preparations of 1,2,3,4-tetrafluoro-5,6-dinitrobenzene and 3,4,5,6-tetrafluoro-1,2-phenylenediamine, and the use of the latter for the synthesis of tetrafluorobenzheterocycles
Journal of Fluorine Chemistry ( IF 1.7 ) Pub Date : 1997 , DOI: 10.1016/s0022-1139(96)03517-8
Alan Heaton , Mark Hill , Frederick Drakesmith

The preparation of 2,3,4,5-tetrafluoro-6-nitroaniline (3) by amination of pentafluoronitrobenzene has been speeded up, scaled up and the yield increased by controlling the reaction by TLC monitoring and using ‘dry column’ chromatography. Compound (3) was readily converted to 1,2,3,4-tetrafluoro-5,6-dinitrobenzene (2) by peroxytrifluoroacetic acid and to 3,4,5,6-tetrafluoro-1,2-phenylenediamine (1) by SnCl2/HCl. Compound (1) was shown to be a versatile intermediate for the synthesis of tetrafluoro-benzimidazoles, -triazoles and -quinoxalines. The fungicidal activity of the latter are reported here.

中文翻译:

聚卤代硝基苯及其衍生化合物第5部分。1,2,3,4-四氟-5,6-二硝基苯和3,4,5,6-四氟-1,2-苯二胺的改进制备方法,以及后者的用途四氟苯并杂环的合成

通过五氟硝基苯的胺化反应,已经加快了制备2,3,4,5-四氟-6-硝基苯胺(3)的规模,扩大了规模,并通过TLC监测和“干柱”色谱法控制了反应,提高了收率。化合物(3)易于通过过氧三氟乙酸转化为1,2,3,4-四氟-5,6-二硝基苯(2),并通过转化为3,4,5,6-四氟-1,2-苯二胺(1)。 SnCl 2 / HCl。化合物(1)被证明是用于合成四氟苯并咪唑,-三唑和-喹喔啉的通用中间体。在此报道了后者的杀真菌活性。
更新日期:2017-01-31
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