About the reaction of aryl fluorides with sodium sulfide: investigation into the selectivity of substitution of fluorobenzonitriles to yield mercaptobenzonitriles via S_NAr displacement of fluorine

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• 作者：Tony Taldone ; ^{taldonet@mskcc.org} ; Pallav D. Patel ^{pallavpatel85@gmail.com} ; Hardik J. Patel ^{PatelH3@mskcc.org} ; Gabriela Chiosis ^{chiosisg@mskcc.org}
• 关键词：Mercaptobenzonitrile ; Aryl fluoride ; SNAr ; Selectivity ; Sodium sulfide
• 刊名：Tetrahedron Letters
• 出版年：2012
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：16 May, 2012
• 卷：53
• 期：20
• 页码：2548-2551
• 文件大小：3111 K

摘要

In this report we describe a simple synthesis of mercaptobenzonitriles from the reaction of fluorobenzonitriles with Na₂S in DMF at room temperature and following direct treatment with Zn/HCl. Significantly, 2- and 4-fluorobenzonitriles substituted with chlorine or bromine, but not iodine, undergo selective substitution of fluorine at room temperature to yield synthetically useful halo-substituted mercaptobenzonitriles.