广东药科大学学报2025，Vol.41Issue(5)：32-36,5.DOI:10.16809/j.cnki.2096-3653.2025060302
异噁唑类化合物中间体3',5'-二氯-4-氟-2,2,2-三氟苯乙酮的合成研究
Study on the synthesis of intermediate 3',5'-dichloro-4-fluoro-2,2,2-trifluorophenone for isoxazole compounds
摘要
Abstract
Object To obtain high-purity isoxazole compound 3',5'-dichloro-4-fluoro-2,2,2-trifluoroacetophenone.Methods Using 4-nitroaniline as the starting material,2,6-dichloro-4-nitroaniline was synthesized via chlorination using chlorosuccinimide.Subsequently,3,4,5-trichloronitrobenzene was obtained through diazotization with sodium nitrite in the presence of cuprous chloride as a catalyst.In the dimethyl sulfoxide solution,3,4,5-trichloronitrobenzene was fluorinated with potassium fluoride to obtain 3,5-dichloro-4-fluoronitrobenzene.Then it was hydrogenated and reduced under the catalysis of Raney nickel to obtain 3,5-dichloro-4-fluoridine.Further diazotization was carried out in hydrogen bromide solution to obtain 3,5-dichloro-4-fluorobenzene.Finally,the target product 3',5'-dichloro 4-fluoro-2,2,2-trifluoroacetophenone was obtained by Grignard reaction with trifluoroacetic acid ethylester.Results 3',5'-Dichloro-4'-fluoro-2,2,2-trifluoroacetophenone was successfully synthesized via a six-step synthetic route,achieving a total yield of 75%.The purity of the target compound was determined to exceed 99%by ¹H NMR spectroscopy.Conclusion The synthesis procedure under mild reaction conditions is straightforward with a relatively high yield,making it suitable for industrial production.关键词
异噁唑化合物/中间体/合成Key words
isoxazole compound/intermediate/synthesis分类
医药卫生引用本文复制引用
余磊,吴子豪,刘安昌,胡勇..异噁唑类化合物中间体3',5'-二氯-4-氟-2,2,2-三氟苯乙酮的合成研究[J].广东药科大学学报,2025,41(5):32-36,5.基金项目
绿色轻工湖北省重点实验室开放项目(202107B06) （202107B06）
