2-氯-4-硝基苯酚的合成新方法

A NEW SYNTHETIC ROUTINE FOR 2-CHLORO-4-NITROPHENOL

采用廉价易得的工业原料2-甲氧基-5-硝基苯胺经重氮化、Sandmeyer反应得2-氯-4-硝基苯甲醚,产物与氢氧化钠发生亲核取代反应,经盐酸水解得到2-氯-4-硝基苯酚,该工艺路线简捷,实用.采用Gaussian 98量子化学程序包对2-氯-4-硝基苯甲醚苯环上各碳原子的Mulliken电荷分布进行计算,结果表明,与甲氧基相连的苯环上5位碳原子Mulliken电荷分布最高,亲核取代反应的位点应在苯环5位碳原子上,量子化学计算预测了实验结果.

By using the economic and easily obtained industrial material 2 - methoxy - 5 - nitroaniline as a starting material, 2 - chloro - 4 - nitroanisole was obtained in the process of diazotization reaction and Sandmeyer reaction. Furthermore, 2 - chloro - 4 - nitroanisole was treated with sodium hydroxide to run a nucleophilic substitution reaction, acidified by hydrochloric acid to give desired product 2 - chloro - 4 - nitrophenol. The synthetic routine i.s simple and appliable. The Mulliken charges of carbons in benzene of 2 - chloro -4 - nitroanisole were calculated by Gaussian 98 program. The results showed that the Mulliken charge of the fifth carbon of benzene connected with methoxy was higher than that of other carbons, which predicts the nucleophilic substitution reaction position.