Synlett 2019; 30(08): 982-986
DOI: 10.1055/s-0037-1611768
letter
© Georg Thieme Verlag Stuttgart · New York

One-Pot Approach for SNAr Reaction of Fluoroaromatic Compounds with Cyclopropanol

Hao Jin
a   Zhejiang Provincial Key Laboratory of Advanced Chemical Engineering Manufacture Technology, College of Chemical and Biological Engineering, Zhejiang University, 38 Zheda Road, Xihu District, Hangzhou, 310000, P. R. of China   Email: qianchao@zju.edu.cn
,
Zhuo Gao
b   Hangzhou Milestone Pharmtech Co. Ltd., 50 Jianshe three road, Xiaoshan District, Hangzhou, 310000, P. R. of China
,
Shaodong Zhou
a   Zhejiang Provincial Key Laboratory of Advanced Chemical Engineering Manufacture Technology, College of Chemical and Biological Engineering, Zhejiang University, 38 Zheda Road, Xihu District, Hangzhou, 310000, P. R. of China   Email: qianchao@zju.edu.cn
,
Chao Qian*
a   Zhejiang Provincial Key Laboratory of Advanced Chemical Engineering Manufacture Technology, College of Chemical and Biological Engineering, Zhejiang University, 38 Zheda Road, Xihu District, Hangzhou, 310000, P. R. of China   Email: qianchao@zju.edu.cn
› Author Affiliations

The authors are grateful for the financial support from the Natural Science Foundation of China (21476194) and the National Key Research and Development Program of China (2016YFB0301800).
Further Information

Publication History

Received: 24 December 2018

Accepted after revision: 07 March 2019

Publication Date:
11 April 2019 (online)


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Abstract

A novel method for preparing aromatic compounds containing cyclopropoxy via nucleophilic aromatic substitution reaction (SNAr) of fluoroaromatic compounds with cyclopropanol under relatively mild conditions is presented. As compared to the approaches reported previously for preparing 1-(cyclopropyloxy)-2-nitrobenzene, the one proposed in this work is simplified without sacrificing the yields: When the reaction was performed at 75 °C with Cs2CO3 as the base and DMF as solvent, after 6 h the yield was up to 90%. Finally, various fluoroaromatic compounds were employed as substrates for a test that proves a wide application scope of the method.

Supporting Information