2-溴-4-硝基苯酚合成的新方法  

Novel method for synthesis of 2-bromo-4-nitrophenol

作　　者：唐天声[1] 王辉[1] 曾卓[1] 廖子英[1] 

机构地区：[1]华南师范大学化学与环境学院,广东广州510006

出　　处：《化学试剂》2008年第4期247-250,共4页Chemical Reagents

基　　金：广东省自然科学基金博士科研启动资助项目(5300410)

摘　　要：以2-甲氧基-5-硝基苯胺为原料经重氮化、Sandmeyer反应得到2-溴-4-硝基苯甲醚,再与氢氧化钠发生亲核取代反应,经盐酸水解得到标题化合物,总收率达55.8%。考察了溶剂和反应物配比对亲核取代反应的影响。该合成路线简便,副产物少,产率高,适合工业化生产。采用Gaussian03量子化学程序包对中间物2-溴-4-硝基苯甲醚中苯环碳原子净电荷的分布进行了计算,结果表明与甲氧基相连的苯环碳原子的净电荷分布最高,预期了亲核取代反应的位点。2-Bromo-4-nitrophenol was synthesized by using 2- methoxy-5-nitroaniline as the starting material via diazotization reaction and the Sandmeyer reaction to yield 2-bromo-4-ni- troanisole, which was further treated with sodium hydroxide to realize a nucleophilic substitution reaction, with the product acidified by hydrochloric acid to obtain the desired product 2-bromo-4- nitrophenol.The target product yield was 55.8%. An optimized process was obtained by investigating the influence of the ratio of solvents and reactants on nucleophilic substitution reaction. The synthetic pathway was simple, efficient and suitable for commer- cial production. The net electric charges of carbons in benzene ring of 2-bromo-4-nitroanisole were calculated by the Gaussian 03 program. The results showed that the net electric charge of carbon in benzene ring connected with methoxy group was the highest than any other, which predicted the nucleophilic substitution reaction position.

关 键 词：2-溴-4-硝基苯甲醚 2-溴-4-硝基苯酚 合成 原子净电荷 

分 类 号：O625.31[理学—有机化学]