Synthesis of ethyl 3-fluoroacrylate from a Tarrant-Stump acetal

Authors
Wakselman, C Molines, H Tordeux, M
Citation
C. Wakselman et al., Synthesis of ethyl 3-fluoroacrylate from a Tarrant-Stump acetal, J FLUORINE, 102(1-2), 2000, pp. 211-213
Citations number
10
Categorie Soggetti
Inorganic & Nuclear Chemistry
Journal title
JOURNAL OF FLUORINE CHEMISTRY
ISSN journal
00221139 → ACNP
Volume
102
Issue
1-2
Year of publication
2000
Pages
211 - 213
Database
ISI
SICI code
0022-1139(200003)102:1-2<211:SOE3FA>2.0.ZU;2-O
Abstract
Diethyl ketal of 3,3-dibromo-3-fluoropropanal was prepared by UV-initiated condensation of fluorotribromomethane with ethyl vinyl ether, following Tar rant-Stump procedure. Direct oxidation of this acetal to ethyl 3,3-dibromo- 3-fluoropropanoate was carried out using Care's acid. On treating this este r with triethylamine, dehydrobromination took place, yielding ethyl 3-bromo -3-fluoroacrylate. Finally, a selective reduction of the bromine atom by tr ibutyltin hydride led to ethyl 3-fluoroacrylate. (C) 2000 Elsevier Science S.A. All rights reserved.