2-bromo-3-chloro-1,4-bis(trimethylsilyl)benzene

• 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-3-chloro-1,4-bis(trimethylsilyl)benzene
• 英文别名: (2-Bromo-3-chloro-4-trimethylsilylphenyl)-trimethylsilane
• 化学式: C₁₂H₂₀BrClSi₂
• 分子量: 335.819
• InChiKey: VSRLLXFLUMZQHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  三甲基氯硅烷 、 2-溴氯苯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以23%的产率得到2-bromo-3-chloro-1,4-bis(trimethylsilyl)benzene
  参考文献：
  名称：

  Bromine as the Ortho-Directing Group in the Aromatic Metalation/Silylation of Substituted Bromobenzenes

  摘要：

  The one-pot metalation/disilylation of selected bromobenzenes bearing electron-withdrawing substituents p-, m-, o-XC6H4Br (X = F, Cl, I, CN, CF3) using 2 equiv of lithium diisopropylamide (LDA) and 2 equiv of chlorotrimethylsilane (TMSCl) was investigated. The best results of disilylation were obtained for para-substituted bromobenzenes, but the regioselectivity of the reaction is strongly influenced by the ortho-directing power of the substituent. On the contrary, the disilylation of meta-substituted bromobenzenes was not efficient or even failed in some cases and hence monosilylated derivatives were isolated as major or sole products. Diverse reactivity was observed for ortho-substituted bromobenzenes, e.g., 2-bromobenzonitrile and 2-bromochlorobenzene, were converted into corresponding disilylated derivatives in a high and moderate yield, respectively, whereas 1-bromo-2-(trifluoromethyl)benzene underwent only monosilylation.

  DOI：

  10.1021/jo034790h

文献信息

• Bromine as the Ortho-Directing Group in the Aromatic Metalation/Silylation of Substituted Bromobenzenes
  作者：Sergiusz Luliński、Janusz Serwatowski

  DOI：10.1021/jo034790h

  日期：2003.11.1

  The one-pot metalation/disilylation of selected bromobenzenes bearing electron-withdrawing substituents p-, m-, o-XC6H4Br (X = F, Cl, I, CN, CF3) using 2 equiv of lithium diisopropylamide (LDA) and 2 equiv of chlorotrimethylsilane (TMSCl) was investigated. The best results of disilylation were obtained for para-substituted bromobenzenes, but the regioselectivity of the reaction is strongly influenced by the ortho-directing power of the substituent. On the contrary, the disilylation of meta-substituted bromobenzenes was not efficient or even failed in some cases and hence monosilylated derivatives were isolated as major or sole products. Diverse reactivity was observed for ortho-substituted bromobenzenes, e.g., 2-bromobenzonitrile and 2-bromochlorobenzene, were converted into corresponding disilylated derivatives in a high and moderate yield, respectively, whereas 1-bromo-2-(trifluoromethyl)benzene underwent only monosilylation.