5-氯-3-氟-2-甲氧基苯甲酸的合成
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摘要
5-氯-3-氟-2-甲氧基苯甲酸是一种抗癌药物中间体取代苯化合物,具有较好的化学和生物活性,未来有望作为医药、农药和染料等精细化学品的重要中间体,目前未见相关研究报道。本文选择以5-氯-2-甲氧基苯甲酸甲酯为起始原料,经过硝化、还原、重氮化、希曼法热解以及水解成酸得到目标化合物,五步总收率达48.39%,相关中间体和目标化合物用HNMR及MS方法进行结构鉴定及确认。
The 5-chloro-3-fluoro-2-methoxybenzoic acid is an anticancer drug intermediate as the substituted benzene compound. It has good chemical and biological activity and is expected to be used as a find chemical in medicine,pesticides and dyes in the future. There is no relevant research report at present. By using methyl 5-chloro-2-methoxybenzoate as original material,the target compound was synthesized through nitration reaction,reduction reaction,diazotization reaction,Blaz-Schieman reaction pyrolysis and hydrolysis reaction with a total yield of 48. 38% in five steps. The related intermediates and target compounds were identified and confirmed by HNMR and MS methods.
The 5-chloro-3-fluoro-2-methoxybenzoic acid is an anticancer drug intermediate as the substituted benzene compound. It has good chemical and biological activity and is expected to be used as a find chemical in medicine,pesticides and dyes in the future. There is no relevant research report at present. By using methyl 5-chloro-2-methoxybenzoate as original material,the target compound was synthesized through nitration reaction,reduction reaction,diazotization reaction,Blaz-Schieman reaction pyrolysis and hydrolysis reaction with a total yield of 48. 38% in five steps. The related intermediates and target compounds were identified and confirmed by HNMR and MS methods.
引文
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[3]邢其毅.基础有机化学[M].北京:高等教育初版社,2005:799-804.
[4]Sexton,Jonathan Z,Brenman et al.Preparation of aryl amides useful for the treatment of metabolic disorders[P].US:20160046560,A1.
[5]宁永成.有机波谱学谱图解析[M].北京:科学出版社,2010:1-32,73-105.
[6]Hewawasam,Piyasena,et al.Preparation of(thiophenyl)triazol-3-ones as smooth muscle relaxants[P].US:20030144333,A1.
[7]Fairfax,David J,Yang Zhicai.Benzoxazloecarboxamides for treating CINV and IBS-D and their Preparation and pharmaceutical[P].US:20060183769,A1.
[8]陈红飙,林原斌.邻氟苯甲腈的合成[J].化学试剂,2002,24(2):103-106.
[9]周晓东.4,4'-二氟二苯甲酮的合成研究[J].精细石油化工进展,2004,5(5):38-41.
[10]徐成治,曽伟,等.2,4-二氟-5-氟甲苯的合成[J].中国医药工业杂志,2001,32(1):31-33.
[11]Bames,Michael Christopher Stratton,et al.Preparation of benzodiazepine derivatives for treating the hepatitis C infection[P].US:20110059043,A1.