期刊
ORGANIC PROCESS RESEARCH & DEVELOPMENT
卷 22, 期 9, 页码 1086-1091出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.oprd.8b00090
关键词
SNAr reaction; calcium fluoride; aryl amines; fluoride sequestration; scale-up
资金
- AstraZeneca
- EPSRC
A simple and operationally practical method to sequester and remove fluoride generated through the SNAr reaction between amines and aryl fluorides is reported. Calcium propionate acts as an inexpensive and environmentally benign in situ scrubber of the hydrofluoric acid byproduct, which is simply precipitated and filtered from the reaction mixture during standard aqueous workup. The method has been tested from 10 to 100 g scale of operation, showing >99.5% decrease in fluoride content in each case. Full mass recovery of calcium fluoride is demonstrated at both scales, proving this to be a general, efficient, and robust method of fluoride abstraction to help prevent corrosion of glass-lined reactors.
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