2-(4-卤代苯甲酰基)苯胺的合成研究

研究了重要的有机中间体2-(4-卤代苯甲酰基)苯胺的通用合成路线,是以邻苯二甲酸酐为原料,与卤代苯(分别为氟苯、氯苯和溴苯)进行付-克反应得到羧酸;羧酸经酰氯化、酰胺化,制得邻苯甲酰基苯甲酰胺衍生物,然后再经过霍夫曼降解合成了标题化合物。对主要步骤反应条件进行了优化,得出比较合理的条件为:付-克反应,催化剂:AlCl3,配料比:1:2.2:6.4(苯酐:AlCl3:卤代苯);同时使用卤代苯既作反应试剂,又作溶剂,未反应的卤代苯回收套用,使收率基本定量;酰胺化反应氨气流量:10mLmin-1,使反应得以室温进行,无需制冷;四步反应总收率可达70%。

Study on the Synthesis of 2-(4-halobenzoyl)aniline

A general synthetic route of 2-(4-halobenzoyl) aniline was proposed which started from phthalic anhydride and halegenated benzene, such as fluorobenzene, chlorobenzene and bromobenzene, via Friedel- Crafts reaction, acid halogenation, amidation and Hoffman degradation to the goal product. The feasible conditions of key steps were investigated. Thus, Friedal-Crafts reaction was conducted by using AlCl3 as catalyst and halegenated benzene as both reaction reagent and solvent with the feed ratio 1:2.2:6.4(phthalic anhydride: AlCl3: halegenated benzene) and unreacted halegenated benzene could be recycled. Amidation was done at room temperature without cooling by means of controlling input flow volume of ammonia at 10mL per minute. The overall yield of synthesis is 70%.