对氨基苯偶酰的合成与表征  

Synthesis and characterization of p-amino benzil

作　　者：任相伟 张万东[1] REN Xiangwei;ZHANG Wandong(School of Science,National Demonstration Center for Experimental Chemistry&Chemical Engineering Education,National Virtual Simulation Experimental Teaching Center for Chemistry&Chemical Engineering Education,Tianjin University,Tianjin 300354,China)

机构地区：[1]天津大学理学院、化学化工国家级实验教学示范中心、化学化工国家级虚拟仿真实验教学中心,天津300354

出　　处：《实验室科学》2022年第6期36-39,共4页Laboratory Science

基　　金：2020年天津市普通高等学校本科教学质量与教学改革研究计划项目(项目编号:B201005607);天津大学实验室建设与管理改革立项项目(项目编号:LAB2018-17);天津大学化学化工国家级实验教学示范中心教学改革与研究项目(项目编号:C20E02;C20E04)。

摘　　要：以α-溴代苯乙酮和苯胺为原料,以I_(2)为催化剂和二甲基亚砜为溶剂的条件下一步合成对氨基苯偶酰,实现了原料的氧化交叉偶联,该方法不使用重金属催化剂,反应条件温和、区域选择性高,具有绿色环保的优点,产物经柱色谱纯化后,通过IR和NMR确证其结构。实验不仅涉及温度控制、薄层色谱、萃取、洗涤、干燥和快速柱色谱的基本操作,还包含了产物的熔点测定和红外、核磁等图谱的采集及解析的实验技能,适合作为高年级本科生的综合实验。A simple,one-step synthesis of p-amine benzil was developed as an organic chemistry laboratory experiment for upper-division undergraduate students.The reaction ofα-bromoacetophenone and aniline in the solvent dimethyl sulfoxide and catalyzed by iodine via direct oxidative cross-coupling afforded the product in higher yield(61%)with high purity by column chromatography.The protocol has the advantages of mild reaction condition,high regioselectivity,and avoiding using heavy metal catalyst,which has the characteristics of green environmental protection.The experiment introduces students to various hands-on experimental organic synthetic techniques,such as temperature control,thin layer chromatography,extraction,washing,drying,flash column chromatography techniques,and characterizing final product by melting point,IR and NMR spectroscopy,which can train the fundamental operation capability of students,and improve their skills interpretation of IR and NMR spectra.

关 键 词：氧化偶联反应 结构表征 有机化学实验 

分 类 号：O621.3[理学—有机化学] G64[理学—化学]