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Simple practical synthesis of 3,3-difluoropyrrolidine from 2,2-dichlorotrifluoro-1-iodoethane
Journal of Fluorine Chemistry ( IF 1.7 ) Pub Date : 2023-12-22 , DOI: 10.1016/j.jfluchem.2023.110236
Andrey B. Koldobskii , Sofia M. Morozova , Olga S. Shilova , Yuri V. Dankov , Sergey K. Moiseev

Novel simple approach was elaborated for the preparation of 3,3-difluoropyrrolidine hydrochloride starting from commercially available technical 2,2-dichlorotrifluoro-1-iodoethane. Its radical addition to ethylene afforded the corresponding iodide that was transformed into the primary amine. The last one was heated with sodium hydrosulfide to form previously unknown 3,3-difluoropyrrolidine-2-thione which was converted into the target product in high yield. The whole transformation does not require the use of toxic, flammable, explosive and hazardous reagents as well as column chromatography purification. Alternative syntheses have been proposed for the intermediate and target compounds.



中文翻译:

由2,2-二氯三氟-1-碘乙烷简单实用合成3,3-二氟吡咯烷

详细阐述了以市售工业品 2,2-二氯三氟-1-碘乙烷为原料制备 3,3-二氟吡咯烷盐酸盐的新颖简单方法。它与乙烯的自由基加成得到相应的碘化物,该碘化物转化为伯胺。最后一种与硫氢化钠一起加热,形成以前未知的3,3-二氟吡咯烷-2-硫酮,并以高产率转化为目标产物。整个转化不需要使用有毒、易燃、易爆等危险试剂,也不需要柱层析纯化。已经提出了中间体和目标化合物的替代合成方法。

更新日期:2023-12-23
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