University Chemistry ›› 2022, Vol. 37 ›› Issue (5): 2110030.doi: 10.3866/PKU.DXHX202110030

Special Issue: 第2届全国大学生化学实验创新设计竞赛

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Optimization and Improvement of "Synthesis of Ethyl 7-Nitrobenzothiophene-2-Carboxylate"

Jiazhu Li(), Yingying Hong, Yingxiu Man, Yinghao Li, Qingzhong Li, Tao He   

  • Received:2021-10-12 Accepted:2021-11-04 Published:2022-03-14
  • Contact: Jiazhu Li E-mail:jiazhu82@ytu.edu.cn

Abstract:

Organic Synthesis Experiment is an important independent experimental course for chemistry students. Current organic synthesis experiments are mostly single-step synthesis, which are insufficient for students' training on connection of multi-step syntheses, compound detection, and identification. Synthesis of ethyl 7-nitrobenzothiophene-2-carboxylate is a comprehensive project in the Organic Synthesis Experiment course for students majoring in applied chemistry at our school; however, it suffers from long reaction times, low yields, difficult work-up, and toxic reagents. This project aims to improve the synthesis methods and procedures of the benzothiophene ring system by reducing the amounts of reagents, increasing the yield, and optimizing the work-up processes. This improved experiment is more suitable as a teaching experiment. Organic spectroscopy was also added in the improved experiment so that students can learn how to characterize target compounds through infrared spectroscopy, nuclear magnetic resonance, and mass spectrometry, which will improve students' comprehension and quality of learning.

Key words: Organic synthesis, Multi-step synthesis, Green chemistry, Benzothiophene

MSC2000: 

  • G64