2-bromo-4-butylthiophene | 350680-78-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 2-bromo-4-butylthiophene
• 英文别名: 2-Bromo-4-butylthiophene
• CAS: 350680-78-3
• 化学式: C₈H₁₁BrS
• 分子量: 219.145
• InChiKey: URYLCIPPKRQTEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-丁基噻吩 在 正丁基锂 、 溴 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.08h， 以90%的产率得到2-bromo-4-butylthiophene
  参考文献：
  名称：

  [EN] A METHOD OF CONTROLLING THE BROMINATION OF THIOPHENE DERIVATIVES
  [FR] PROCÉDÉ PERMETTANT DE MAÎTRISER LA BROMATION DE DÉRIVÉS DE THIOPHÈNE

  摘要：

  提供了一种改进产量的卤代烷基噻吩的区域选择性合成方法。将3-烷基噻吩在-78°C下用n-BuLi激活约1.5小时，然后与溴反应，得到具有良好区域选择性的卤代烷基噻吩。

  公开号：

  WO2011155679A1

文献信息

• A selective and direct synthesis of 2-bromo-4-alkylthiophenes: Convenient and straightforward approaches for the synthesis of head-to-tail (HT) and tail-to-tail (TT) dihexyl-2,2′-bithiophenes
  作者：Ashraf A. El-Shehawy、Nabiha I. Abdo、Ahmed A. El-Barbary、Jae-Suk Lee

  DOI：10.1016/j.tetlet.2010.06.100

  日期：2010.8

  A straightforward method for the synthesis of 2-bromo-4-alkylthiophenes was developed, and the desired products were obtained in the highest chemical yields (>90%) reported to date. 2-Bromo-4-alkylthiophenes were synthesized by regioselective lithiating of 3-alkylthiophenes with n-BuLi and quenching with bromine at 78 degrees C. Moreover, a simple and efficient protocol for the synthesis of dihexyl-2,2'-bithiophenes was developed by employing 2-bromo-4-hexylthiophene instead of the commonly used monomer, 2-bromo-3-hexylthiophene. Kumada and Suzuki cross-coupling reactions were conducted to synthesize the desired products as head-to-tail (HT) and tail-to-tail (TT) regioisomers in high yields and excellent selectivity. (C) 2010 Elsevier Ltd. All rights reserved.