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Synthesis of ethyl 3-fluoroacrylate from a Tarrant–Stump acetal
Journal of Fluorine Chemistry ( IF 1.7 ) Pub Date : 2000 , DOI: 10.1016/s0022-1139(99)00281-x
Claude Wakselman , Huguette Molines , Marc Tordeux

Diethyl ketal of 3,3-dibromo-3-fluoropropanal was prepared by UV-initiated condensation of fluorotribromomethane with ethyl vinyl ether, following Tarrant–Stump procedure. Direct oxidation of this acetal to ethyl 3,3-dibromo-3-fluoropropanoate was carried out using Caro’s acid. On treating this ester with triethylamine, dehydrobromination took place, yielding ethyl 3-bromo-3-fluoroacrylate. Finally, a selective reduction of the bromine atom by tributyltin hydride led to ethyl 3-fluoroacrylate.

中文翻译:

用塔兰特-树桩缩醛合成3-氟丙烯酸乙酯

按照Tarrant–Stump程序,通过紫外引发的氟代三溴甲烷与乙基乙烯基醚的缩合反应制得3,3-二溴-3-氟丙醛的二乙基缩酮。使用卡罗酸将该缩醛直接氧化为3,3-二溴-3-氟丙酸乙酯。用三乙胺处理该酯后,发生脱氢溴化反应,得到3-溴-3-氟丙烯酸乙酯。最后,通过氢化三丁基锡选择性地还原溴原子,得到3-氟丙烯酸乙酯。
更新日期:2017-01-31
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