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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 7
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Original Articles

Direct Perfluorination of an Acid-Sensitive Glycol Ether as Precursor for Perfluoro(2-(methoxymethoxy)ethyl Vinyl Ether)

Hongle Liu Key Laboratory for Radiation Physics and Technology of Ministry of Education, College of Chemistry, Nuclear Institute of Science and Technology, Sichuan University, Chengdu, China
,
Xusong Pan Key Laboratory for Radiation Physics and Technology of Ministry of Education, College of Chemistry, Nuclear Institute of Science and Technology, Sichuan University, Chengdu, China
,
Lihua Yuan Key Laboratory for Radiation Physics and Technology of Ministry of Education, College of Chemistry, Nuclear Institute of Science and Technology, Sichuan University, Chengdu, China
,
Shuliang Zou Key Laboratory for Radiation Physics and Technology of Ministry of Education, College of Chemistry, Nuclear Institute of Science and Technology, Sichuan University, Chengdu, China
,
Peishen Li Key Laboratory for Radiation Physics and Technology of Ministry of Education, College of Chemistry, Nuclear Institute of Science and Technology, Sichuan University, Chengdu, China
,
Wei Wang Key Laboratory for Radiation Physics and Technology of Ministry of Education, College of Chemistry, Nuclear Institute of Science and Technology, Sichuan University, Chengdu, China
,
Youzhou He Key Laboratory for Radiation Physics and Technology of Ministry of Education, College of Chemistry, Nuclear Institute of Science and Technology, Sichuan University, Chengdu, China
,
Wen Feng Key Laboratory for Radiation Physics and Technology of Ministry of Education, College of Chemistry, Nuclear Institute of Science and Technology, Sichuan University, Chengdu, ChinaCorrespondence[email protected]
,
Xiaoyong Yang Zhong Lan Chenguang Research Institute of Chemical Industry, Chengdu, ChinaCorrespondence[email protected]
,
Kai Luo Zhong Lan Chenguang Research Institute of Chemical Industry, Chengdu, China
&
Yong Wu Zhong Lan Chenguang Research Institute of Chemical Industry, Chengdu, China
 show all
Pages 959-966 | Received 23 Apr 2010, Published online: 16 Dec 2011
 
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Abstract

A four-step approach to perfluoro(2-(methoxymethoxy)ethyl vinyl ether) 5 from an acid-sensitive glycol ether 3 by liquid-phase direct fluorination (DF) has been described. The perfluoro precursor was achieved by control of the gradient increase of temperature (−20 °C to 15 °C) and addition of sodium fluoride. Improved workup with benzyl alcohol provided a convenient method for purification and a practical means for tracing the progress of fluorination.

GRAPHICAL ABSTRACT

ACKNOWLEDGMENTS

The authors thank Chenguang Research Foundation and the Analytical and Testing Center of Sichuan University for NMR analysis. Thanks are also extended to Guowei Yang and Fumin Hu for helpful discussions.

Notes

a Yield was based on methyl ester 4b obtained from addition of methanol to 4a and determined by the distilled fraction. Identity of each fraction was confirmed by 1H NMR characterization.

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