二氟芳烃衍生物的合成研究-有机化学专业论文.docxVIP

Abstract Difluoro aromatic derivatives are a kind of important intermediates for the synthesis of fine chemicals. They are widely used for the preparation of pesticide and pharmaceutical. The synthesis of difluoro aromatic derivatives is highly regarded in organic synthesis. The novel methods for the synthesis of difluoro aromatic derivatives are reported in this thesis. One approach is that difluorobenzonitrile is prepared from chlorobenzonitrile through nitration, fluorination, reduction, diazotization followed by Schiemann reaction. Another method is that a series of difluoro aromatic compounds are chloromethylated followed by transformation of chloromethyl to corresponding difluoro aromatic derivatives. Additionaly, the influence factors of the reaction have also been studied. In comparison to what described in the literatures, the former method has the following advantages: easily obtained materials, mild reaction conditions, simple work-up procedure, high yields and easily to enlarge. The latter method is superior in short step, simple work-up and high efficiency. A series of difluoro aromatic derivatives have been synthesized through the novel approaches, such compounds include 2,5-difluorobenzonitrile, 3,4-difluorobenzonitrile, 3,4-difluorobenzyl chloride, 2,5-difluorobenzyl chloride, 2,4-difluorobenzyl chloride, 1,5-dichloromethyl-2,4-difluorobenzene, 3,4-difluorobenzoic acid, 2,5-difluorobenzoic acid, 2,4-difluorobenzoic acid, 1,5-dicarboxyl-2,4-difluorobenzene, 3,4-difluorobenzal- dehyde, 2,5-difluorobenzaldehyde, 2,4-difluorobenzaldehyde, 3,4-difluorobenzyl alcoh- ol, 2,5-difluorobenzyl alcohol, 2,4-difluorobenzyl alcohol, 3,4-difluorobenzylamine, 2,5-difluorobenzylamine, 2,4-difluorobenzylamine, 3,4-difluoroacetophenone, 2,5-di- fluoroacetophenone and 2,4-difluoroacetophenone. The compounds were characterized by NMR spectroscopy. The novel methods are universal in organic synthesis, which can be utilized to synthesize other difluoro aromatic derivative