3-氯-2-硝基苯乙腈的合成研究

Study on Synthesis of 3-Chloro-2-nitrophenylacetonitrile

由2,6-二氯硝基苯与氰乙酸叔丁酯反应制备了2-氰基-2-(3′-氯-2′-硝基苯基)乙酸叔丁酯(1),在对甲苯磺酸催化作用下,由化合物(1)脱羧制备了3-氯-2-硝基苯乙腈。考查了不同反应时间、反应温度及摩尔比对目标产物产率的影响。较佳的合成条件为:n[2-氰基-2-(3′-氯-2′-硝基苯基)乙酸叔丁酯]∶n(对甲苯磺酸.H2O)=1∶0.075,反应时间2 h,反应温度100°C,产物收率可达89%以上。化合物结构经IR、1H NMR、MS进行了表征。

Tert-butyl 2-cyano-2（3-chloro-2-nitrophenyDacetate was prepared from 2,6-dichloronitrobenzene and tert-butyl cyanoacetate. 3-chloro-2-nitro benzyl cyanide was further synthesized using tert-butyl 2- cyano-2（3-chloro-2-nitrophenyl） acetate as raw material and paratoluenesulfonie acid as catalyst by decarboxylic reaction. The effects of feed composition, reaction temperature and reaction time on the yield of 3-chloro-2-niro benzyl cyanide were investigated. The optimized conditions was： n[tert-butyl 2-cyano-2 （3-chloro-2-nitrophenyl） acetate] ： n（paratoluenesulfonic acid）= 1 ： 0. 075; temperature, 100℃; and reaction time, 2 h. The yield of 3-chloro-2-nitro benzyl cyanide reached 89. 3%. The product was characterized by IR, ^1H NMR and MS.