Suzuki偶联反应合成1,3,5-三(4-甲基苯基)苯
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摘要
以三溴苯、对甲基苯硼酸和K_2CO_3为反应原料,N,N-二甲基甲酰胺为溶剂,钯碳为催化剂,通过Suzuki偶联反应制备1,3,5-三(4-甲基苯基)苯。采用核磁共振氢谱和碳谱分析、红外光谱分析及元素分析对所制产物进行了表征,确定了产物为1,3,5-三(4-甲基苯基)苯,该反应的产率约为31%。
In this thesis, 1,3,5-tris(4-methylphenyl)benzene(BTB) was synthesized through Suzuki coupling reaction, using 1,3,5-tribromo-benzene, 4-methylphenylboronic acid and potassium carbonate as raw materials, N,N-dimethyl formamide as solvent, palladium carbon as catalyst. The molecular structure of the prepared product was identified by nuclear magnetic resonance spectroscopy(NMR),Fourier Transform Infrared Spectroscopy(FTIR)and elemental analysis. The results showed that the product was 1,3,5-tris(4-methylphenyl)benzene with a relatively high purity, the yield was about 31%.
In this thesis, 1,3,5-tris(4-methylphenyl)benzene(BTB) was synthesized through Suzuki coupling reaction, using 1,3,5-tribromo-benzene, 4-methylphenylboronic acid and potassium carbonate as raw materials, N,N-dimethyl formamide as solvent, palladium carbon as catalyst. The molecular structure of the prepared product was identified by nuclear magnetic resonance spectroscopy(NMR),Fourier Transform Infrared Spectroscopy(FTIR)and elemental analysis. The results showed that the product was 1,3,5-tris(4-methylphenyl)benzene with a relatively high purity, the yield was about 31%.
引文
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[3]Jialiu Ma,Antek G.Wong-Foy,and Adam J.Matzger.The Role of Modulators in Controlling Layer Spacings in a Tritopic Linker Based Zirconium 2D Microporous Coordination Polymer[J].Inorg.Chem.,2015,54:4591-4593.
[4]Guo Ping Zhang,Ren Hua Qiu,Xin Hua Xu,Hai Hui Zhou,Ya Fei Kuang,and Si Hai Chen.Zirconocene Bis(perfluorooctanesulfonate)s-Catalyzed Highly Efficient Synthesis of 1,3,5-Triaryl Benzene via Cyclotrimerization of Ketones[J].Synthetic Communications,2012,42:858-864.
[5]Huanan Hu,Anjiang Zhang,Lisheng Ding,Xinxiang Lei and Lixue Zhang.Simple and convenient synthesis of 1,3,5-triarylbenzengs from ketones[J].Journal of chemical research,2007:720-721.
[6]Yanli Xu,Yingming Pan,Qiang Wu,Hengshan Wang,and Pei-zhen Liu.Regioselective Synthesis of 1,3,5-Substituted benzenes via the In Cl3/2-lodophenol-Catalyzed Cyclotrimerization of Alkynes[J].J.Org.Chem.,2011,76:8472-8476.
[7]Jinheng Li,Yeciang Xie.Carbon Dioxide Promoted Palladium Catalyzed Cyclotrimerization of Alkynes in Water[J].Synthetic Communications,2004,34:1737-1743.
[8]The University of Tokyo Patent:WO:2006/85628 A1,2006.
[2]Dongwook Kim,Xiaokai Song,Jung Hee Yoon,and Myoung Soo Lah.3,6-Connected Metal Organic Frameworks Based on Triscarboxylate as a 3-Connected Organic Node and a Linear Trinuclear Co3(COO)6Secondary Building Unit as a 6-Connected Node.Cryst[J].Growth Des.,2012,(12):4186-4193.
[3]Jialiu Ma,Antek G.Wong-Foy,and Adam J.Matzger.The Role of Modulators in Controlling Layer Spacings in a Tritopic Linker Based Zirconium 2D Microporous Coordination Polymer[J].Inorg.Chem.,2015,54:4591-4593.
[4]Guo Ping Zhang,Ren Hua Qiu,Xin Hua Xu,Hai Hui Zhou,Ya Fei Kuang,and Si Hai Chen.Zirconocene Bis(perfluorooctanesulfonate)s-Catalyzed Highly Efficient Synthesis of 1,3,5-Triaryl Benzene via Cyclotrimerization of Ketones[J].Synthetic Communications,2012,42:858-864.
[5]Huanan Hu,Anjiang Zhang,Lisheng Ding,Xinxiang Lei and Lixue Zhang.Simple and convenient synthesis of 1,3,5-triarylbenzengs from ketones[J].Journal of chemical research,2007:720-721.
[6]Yanli Xu,Yingming Pan,Qiang Wu,Hengshan Wang,and Pei-zhen Liu.Regioselective Synthesis of 1,3,5-Substituted benzenes via the In Cl3/2-lodophenol-Catalyzed Cyclotrimerization of Alkynes[J].J.Org.Chem.,2011,76:8472-8476.
[7]Jinheng Li,Yeciang Xie.Carbon Dioxide Promoted Palladium Catalyzed Cyclotrimerization of Alkynes in Water[J].Synthetic Communications,2004,34:1737-1743.
[8]The University of Tokyo Patent:WO:2006/85628 A1,2006.