玉米田除草剂环磺酮的合成  

Synthesis of Herbicide Tembotrione in Corn Field

作　　者：余玉[1] 苏建宇[1] 董元海 郑怡倩 汪鲁焱 刘安昌[1] 

机构地区：[1]武汉工程大学化工与制药学院,武汉430074

出　　处：《农药》2017年第5期326-327,379,共3页Agrochemicals

摘　　要：[目的]旨在探索一条适合工业化生产环磺酮的工艺路线。[方法]以3-氯-2-甲基苯胺和甲硫醇钠为起始原料,在亚硝酸钠的作用下得到2-氯-6-甲巯基甲苯,然后和乙酰氯发生酰化反应,再经过氧化氢氧化后,与次氯酸钠发生卤仿反应得到2-氯-3-甲基-4-甲磺酰基苯甲酸;最后经过酯化和溴化反应得到2-氯-3-溴甲基-4-甲磺酰基苯甲酸甲酯使之与三氟乙醇发生取代反应,水解后得到最终产物2-氯-3-(2,2,2-三氟乙氧基)甲基-4-甲磺酰基苯甲酸;在丙酮氰醇的催化下,2-氯-3-(2,2,2-三氟乙氧基)甲基-4-甲磺酰基苯甲酸与1,3-环己二酮反应得到目的产物环磺酮。[结果]经1H NMR光谱鉴定,产品结构与环磺酮结构一致。[结论]该工艺简单经济,条件温和,适合工业化生产。[Aims] This article aims to explore and optimize a reasonable route of tembotrione on industrial scale. [Methods] 2-Chloro-6-methylmercaptotoluene was obtained by the reaction of sodium nitrite, 3-chloro-2-methylaniline and sodium methanethiol, followed by acylation with acetyl chloride. 2-Chloro-3-methyl-4-methanesulfonylbenzoic acid was obtained after oxidation with hydrogen peroxide and then halogenation reaction with sodium hypochlorite. Finally, 2-chloro-3-bromomethyl-4 -methylsulfonylbenzoic acid methyl ester was reacted with trifluoroethanol to give 2-chloro-3-（2,2,2-trifluoroethoxy）methyl-4-methanesulfonyl benzoic acid; in the presence of acetone cyanohydrin, 2-chloro-3-（2,2,2-trifluoroethoxy）methyl-4-methanesulfonyl benzoic acid was reacted with cyclohexanedione to afford the target product oftembotrione. [Results] The obtained product was identified with 1H NMR. [Conclusions] This process is simple, warm and economical, which is suitable for industrial manufacture.

关 键 词：环磺酮 除草剂 合成 

分 类 号：TQ457.2[化学工程—农药化工]