2,3,4,5-四氟苯甲酸的合成  

The Synthesis of 2,3,4,5-Tetrafluorobenzoic Acid

作　　者：陈坤[1] 胡传群[2] 

机构地区：[1]湖北工业大学科技与产业处,湖北武汉430068 [2]湖北工业大学化学与环境工程学院,湖北武汉430068

出　　处：《湖北工业大学学报》2006年第2期6-8,共3页Journal of Hubei University of Technology

摘　　要：以N-苯基-四氯邻苯二甲酰亚胺（PDPA）为起始原料，合成了第三代喹诺酮类抗菌药物的重要中间体2，3，4，5-四氟苯甲酸（TFBA）．DMF作溶剂，十六烷基三丁基溴化铵为相转移催化剂，PDPA与氟化钾在140～150℃反应7～9h，得到N-苯基-四氟邻苯二甲酰亚胺（PTFP），收率87％；在十六烷基三甲基溴化铵催化下，用1．5mol／L氢氧化钾溶液开环PTFP，获得N-苯基-2-羧基-3，4，5，6-四氟苯甲酰胺（PCTFBA），收率98％；PCTFBA分别在N，N-二甲基乙醇胺、硫酸-乙酸溶液中完成脱羧和水解反应，收率依次为76％、87％．反应工艺简单，反应条件平和，TFBA总收率高达56．4％．2,3,4,5-Tetrafluorobenzoic acid （TFBA）, an important intermediates of fluoroquinolone antibiotics, was prepared starting from N-phenyl tetrachlorophthalimide, which reacted with potassium fluoride in the presence of DMF and hexadecyltributylammonium bromide at 140-150℃ for 7-9 h to give N-phenyl tetrafluorophthalimide （PTFP） in 87% yield. Open-ring of PTFP in 1.5 mol/L potassium hydrate with hexadecyltrimethylammonium bromide as catalyst gave N-phenyl-2-carboxy-3,4,5,6- tetrafluorobenzoyl amine（PCTFBA） in 98% yield, and deearboxylation of PCTFBA with N,N-dimethyl-ethylolamine as solvent gave N-phenyl -2,3,4,5-tetrafluorobenzoyl amine （PTFBA） in 76% yield; after hydrolysis, TFBA was obtained in 87% yield. The reactions of all steps were carried out in moderate condition to afford the total yield of TFBA up to 56.4%.

关 键 词：2 3 4 5-四氟苯甲酸 N-苯基-四氯邻苯二甲酰亚胺 喹诺酮类抗菌药物 

分 类 号：TQ463[化学工程—制药化工]