2-bromo-N-(2,6-dimethylphenyl)benzamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-bromo-N-(2,6-dimethylphenyl)benzamide
• 英文别名: 2-bromo-N-(2,6-diisopropylphenyl)benzamide；2-bromo-N-[2,6-di(propan-2-yl)phenyl]benzamide
• 化学式: C₁₉H₂₂BrNO
• 分子量: 360.294
• InChiKey: JNJSBZLNMDZEQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  邻碘溴苯 、 一氧化碳 、 2,6-二异丙基苯胺 在 二(三叔丁基膦)钯 、 四丁基氯化铵 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 20.0 ℃ 、204.75 kPa 条件下， 反应 20.0h， 以94%的产率得到2-bromo-N-(2,6-dimethylphenyl)benzamide
  参考文献：
  名称：

  A Palladium-Catalyzed Carbonylation Approach to Acid Chloride Synthesis

  摘要：

  We describe a new approach to acid chloride synthesis via the palladium-catalyzed carbonylation of aryl iodides. The combination of sterically encumbered phosphines ((PBu3)-Bu-t) and CO coordination has been found to facilitate the rapid carbonylation of aryl iodides into acid chlorides via reductive elimination from ((Bu3P)-Bu-t)(CO)Pd(COAr)Cl. The formation of acid chlorides can also be exploited to perform traditional aminocarbonylation reactions under exceptionally mild conditions (ambient temperature and pressure), and with a range of weakly nucleophilic substrates.

  DOI：

  10.1021/ja4098093

文献信息

• A Palladium-Catalyzed Carbonylation Approach to Acid Chloride Synthesis
  作者：Jeffrey S. Quesnel、Bruce A. Arndtsen

  DOI：10.1021/ja4098093

  日期：2013.11.13

  We describe a new approach to acid chloride synthesis via the palladium-catalyzed carbonylation of aryl iodides. The combination of sterically encumbered phosphines ((PBu3)-Bu-t) and CO coordination has been found to facilitate the rapid carbonylation of aryl iodides into acid chlorides via reductive elimination from ((Bu3P)-Bu-t)(CO)Pd(COAr)Cl. The formation of acid chlorides can also be exploited to perform traditional aminocarbonylation reactions under exceptionally mild conditions (ambient temperature and pressure), and with a range of weakly nucleophilic substrates.