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含氟芳香族化合物是一类重要的芳香族化合物，由于氟原子电负性强及原子半径小，其具有很多独特的性质，在生物化学、医药、农药、功能材料和染料等领域中具有广泛的应用价值。将CF3基引入底物可以使目标化合物极性增强、稳定性和亲油性提高，是合成医药、农药等的重要中间体，对其合成研究及开发有着相当广阔的前景。 本课题主要研究了2,6-二氯-4-三氟甲基苯胺、4-三氟甲基苯乙醇、4-三氟甲基苯乙酸、2,5-二氯-4-三氟甲基氯苄的合成，其中2,5-二氯-4-三氟甲基氯苄的合成及应用国内外未见报道，且没有CAS号。主要工艺及成果如下： (1)以4-三氟甲基苯胺为原料，在65℃、盐酸-双氧水体系中进行氯化反应制备2,6-二氯-4-三氟甲基苯胺，收率94.7%。并对产品的结构进行IR、1H NMR表征。 (2)研究了一种制备4-三氟甲基苯乙醇的新方法，以4-三氟甲基苯胺为原料，经重氮化、Sandmeyer反应制得4-三氟甲基溴苯，收率93.3%，再经Grignard反应制得4-三氟甲基苯乙醇，收率85.5%。以4-三氟甲基苯胺计，两步反应的总收率79.8%。 (3)研究了一种制备4-三氟甲基苯乙酸的新方法，以4-三氟甲基苯胺为原料，经重氮化、Sandmeyer反应制得4-三氟甲基溴苯，后经Grignard反应制得4-三氟甲基苯乙酮酸乙酯，再经Wolff-Kishner黄鸣龙还原反应得4-三氟甲基苯乙酸。以4-三氟甲基苯胺计，三步反应的总收率68.4%。 (4)探讨了一种2,5-二氯-4-三氟甲基氯苄的合成方法，4-三氟甲基苯胺为原料，经重氮化、Sandmeyer反应制得4-三氟甲基溴苯，经Bouveault醛合成得4-三氟甲基苯甲醛，再经KBH4还原为4-三氟甲基苯甲醇，与SOCl2和氯气氯化反应制得2,5-二氯-4-三氟甲基氯苄。以4-三氟甲基苯胺计，五步反应的总收率22%。 |
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zj19820305
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| Aromatic fluorine compounds, an important aromatic species, possess many unique properties due to the stronger electronegativity and smaller size in the radius of fluorine atom. And they have wide applications in the fields of biological chemistry, medicine, pesticide, funtional materials and dyes, and so on. The introduction of CF3 group could improve the polarity, stability and lipophilicity of the target compound, which is the important intermediate of the synthesization of medicine and pesticide, and has considerably extensive potential in the research and development of synthesizing. |
2楼2009-04-02 09:33:30
zj19820305
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本课题主要研究了2,6-二氯-4-三氟甲基苯胺、4-三氟甲基苯乙醇、4-三氟甲基苯乙酸、2,5-二氯-4-三氟甲基氯苄的合成，其中2,5-二氯-4-三氟甲基氯苄的合成及应用国内外未见报道，且没有CAS号。主要工艺及成果如下： This subject is focused on the synthesizations of 2, 6-dichloro-4-trifluoromethylaniline, 4-trifluoromethylphenylethanol, 4-trifluoromethyphenylacetic acid, 2,5-dichloro-4-trifluoromethylbenzyl chloride. Among them, the synthesizing and application of 2,5-dichloro-4-trifluoromethylbenzyl chloride has not been repoted in domestic and overseas, and there has not also CAS number so far. The main technology and the results are as follows: |
3楼2009-04-02 09:51:11
zj19820305
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1) 4-trifluoromethlyaniline as the start material, the chlorination reaction was performed in hydrochloride-hiydrogen peroxide system at 65℃ to produce 2, 6-dichloro-4-trifluoromethylaniline, the productivity of which was 94.7%. And the structure of the product was characterized by IR and NMR. 2) A new method for preparing 4-trifluoromethylphenylethanol was developed. 4-trifluoromethlyaniline as the start material, 4-trifluoromethylphenyl bromide was obtained through diazotization and Sandmeyer reaction with the yield of 93.3%, and then by Grignard reaction, 4-trifluoromethylphenylethanol was prepared with the yield of 85.5%. The overal yield was 79.8% calculated with 4-trifluoromethlyaniline. |
4楼2009-04-02 10:13:47
zj19820305
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3) A new method for preparing 4-trifluoromethyphenylacetic acid was studied. 4-trifluoromethlyaniline as the start material, 4-trifluoromethylphenyl bromide was obtained through diazotization and Sandmeyer reaction, and then 4-trifluoromethyl phenyl glyoxilic ethyl ester was prepared by Grignard reaction, and followingly, Wolff-Kishner4-trifluoromethyp-Huangminglong reaction was performed to prepare 4-trifluoromethyphenylacetic acid. The overal yield of the three step reaction was 68.4% calculated with 4-trifluoromethlyaniline. 4) A method for preparing 2,5-dichloro-4-trifluoromethylbenzyl chloride was explored. 4-trifluoromethlyaniline as the start material, 4-trifluoromethlyaniline as the start material, 4-trifluoromethylphenyl bromide was obtained through diazotization and Sandmeyer reaction, and by bouveault aldehyde condensation, 4-trifluoromethyl phenylaldehyde was obtained. Then it was reduced by KBH4 to be 4-trifluoromethyl benzyl methanol, which was reacted with SOCl2 and Cl2 to produce 2,5-dichloro-4-trifluoromethylbenzyl chloride by chlorination raction. The overal yield was 22% calculated with 4-trifluoromethlyaniline. |
5楼2009-04-02 10:32:23
zj19820305
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6楼2009-04-02 10:34:04
