3-bromo-4-(p-tolylthio)pyridine

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-bromo-4-(p-tolylthio)pyridine
• 英文别名: 3-Bromo-4-(4-methylphenyl)sulfanylpyridine；3-bromo-4-(4-methylphenyl)sulfanylpyridine
• 化学式: C₁₂H₁₀BrNS
• 分子量: 280.188
• InChiKey: PFYOPGVIGDNUSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-溴-4-硝基吡啶 、 4-甲苯硫酚 在 potassium phosphate 、 18-冠醚-6 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以88%的产率得到3-bromo-4-(p-tolylthio)pyridine
  参考文献：
  名称：

  C-S coupling with nitro group as leaving group via simple inorganic salt catalysis

  摘要：

  An efficient and practical synthetic protocol to synthesize nonsymmetrical aryl thioethers by nucleophilic aromatic substitution (SNAr) reaction of nitroarenes by thiols with potassium phosphate as the catalyst is described. Various moderate to strong electron-withdrawing functional groups are tolerated by the system to provide thioethers in a good to excellent yields. We also showed that the present method allows access to 3 drug examples in a short reaction time. Finally, mechanistic studies suggest that the reaction may form the classic Meisenheimer complex through a two-step addition elimination mechanism. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2019.07.012

文献信息

• C-S coupling with nitro group as leaving group via simple inorganic salt catalysis
  作者：Maojie Xuan、Chunlei Lu、Bo-Lin Lin

  DOI：10.1016/j.cclet.2019.07.012

  日期：2020.1

  An efficient and practical synthetic protocol to synthesize nonsymmetrical aryl thioethers by nucleophilic aromatic substitution (SNAr) reaction of nitroarenes by thiols with potassium phosphate as the catalyst is described. Various moderate to strong electron-withdrawing functional groups are tolerated by the system to provide thioethers in a good to excellent yields. We also showed that the present method allows access to 3 drug examples in a short reaction time. Finally, mechanistic studies suggest that the reaction may form the classic Meisenheimer complex through a two-step addition elimination mechanism. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.