2-溴-4-硝基乙酸苯酯 | 63801-96-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 中文名称: 2-溴-4-硝基乙酸苯酯
• 英文名称: 2-bromo-4-nitrophenyl acetate
• 英文别名: (2-bromo-4-nitrophenyl) acetate
• CAS: 63801-96-7
• 化学式: C₈H₆BrNO₄
• 分子量: 260.044
• InChiKey: QIKPOTVKYGFMHN-UHFFFAOYSA-N

物化性质

• 沸点：
  340.9±32.0 °C(Predicted)
• 密度：
  1.676±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2915390090

反应信息

• 作为反应物：
  描述：

  2-溴-4-硝基乙酸苯酯 在 bis-triphenylphosphine-palladium(II) chloride 、 三乙胺 、 苯乙炔 作用下， 反应 24.0h， 生成 2-溴-4-硝基苯酚
  参考文献：
  名称：

  Efficient synthesis of 5-nitro-benzo[b]furans via 2-bromo-4-nitro-phenyl acetates

  摘要：

  Acetylation/Sonogashira cross-coupling reaction/cyclization has been carried out in one-pot using a Na2PdCl4/2-(di-tert-butylphosphino)-N-phenylindole/Cul system in TMEDA to give 5-nitro-2-substituted benzo[b]furans in excellent yields. We also describe the extension of this method to 4-EWG-2-bromophenols obtaining 2,5-disubstituted-benzo[b]furans in good yields. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.03.072
• 作为产物：
  描述：

  乙酰溴 、 2-溴-4-硝基苯酚 在 四甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 生成 2-溴-4-硝基乙酸苯酯
  参考文献：
  名称：

  Efficient synthesis of 5-nitro-benzo[b]furans via 2-bromo-4-nitro-phenyl acetates

  摘要：

  Acetylation/Sonogashira cross-coupling reaction/cyclization has been carried out in one-pot using a Na2PdCl4/2-(di-tert-butylphosphino)-N-phenylindole/Cul system in TMEDA to give 5-nitro-2-substituted benzo[b]furans in excellent yields. We also describe the extension of this method to 4-EWG-2-bromophenols obtaining 2,5-disubstituted-benzo[b]furans in good yields. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.03.072

文献信息

• Synthesis of Benzofuropyridines and Dibenzofurans by a Metalation/Negishi Cross-Coupling/S_NAr Reaction Sequence
  作者：Guy J. Clarkson、Stefan Roesner

  DOI：10.1021/acs.joc.2c02111

  日期：2023.1.6

  methodology for the synthesis of benzofuropyridines and dibenzofurans from fluoropyridines or fluoroarenes and 2-bromophenyl acetates is reported. This streamlined one-pot procedure consists of a four-step directed ortho-lithiation, zincation, Negishi cross-coupling, and intramolecular nucleophilic aromatic substitution, allowing for the facile assembly of a diverse set of fused benzofuro heterocycles.

  报道了一种从氟吡啶或氟芳烃和乙酸 2-溴苯酯合成苯并呋喃吡啶和二苯并呋喃的有效方法。这种简化的一锅法程序包括四步定向邻位锂化、锌化、Negishi 交叉偶联和分子内亲核芳族取代，允许轻松组装一组不同的稠合苯并呋喃杂环。
• Aryloxenium ions. Generation from N-(aryloxy)pyridinium tetrafluoroborates and reaction with anisole and benzonitrile
  作者：Rudolph A. Abramovitch、Gerard Alvernhe、Romuald Bartnik、Nissanke L. Dassanayake、Mutiah N. Inbasekaran、Shiego Kato

  DOI：10.1021/ja00405a043

  日期：1981.7
• van Erp, Recueil des Travaux Chimiques des Pays-Bas, 1910, vol. 29, p. 230
  作者：van Erp

  DOI：——

  日期：——
• ABRAMOVITCH R. A.; ALVERNHE G.; BARTNIK R.; DASSANAYAKE N. L.; INBASEKARA+, J. AMER. CHEM. SOC., 1981, 103, NO 15, 4558-4565
  作者：ABRAMOVITCH R. A.、 ALVERNHE G.、 BARTNIK R.、 DASSANAYAKE N. L.、 INBASEKARA+

  DOI：——

  日期：——
• Efficient synthesis of 5-nitro-benzo[b]furans via 2-bromo-4-nitro-phenyl acetates
  作者：Antonella Bochicchio、Lucia Chiummiento、Maria Funicello、Maria Teresa Lopardo、Paolo Lupattelli

  DOI：10.1016/j.tetlet.2010.03.072

  日期：2010.5

  Acetylation/Sonogashira cross-coupling reaction/cyclization has been carried out in one-pot using a Na2PdCl4/2-(di-tert-butylphosphino)-N-phenylindole/Cul system in TMEDA to give 5-nitro-2-substituted benzo[b]furans in excellent yields. We also describe the extension of this method to 4-EWG-2-bromophenols obtaining 2,5-disubstituted-benzo[b]furans in good yields. (C) 2010 Elsevier Ltd. All rights reserved.