Method for preparing aromatic cross-coupled compound
A cross-coupling and compound technology, which is applied in the field of preparation of aromatic cross-coupling compounds, can solve the problems that aryl diazonium salts are difficult to obtain, limit the application of coupling reactions, and are sensitive to heat and light, and achieves low cost and substrates. Stable, well-tolerated effect
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Embodiment 1
[0029] Synthesis of 4-methoxybiphenyl
[0030] Add 182mg (i.e. 1.2mmol) p-methoxyphenylboronic acid, 23mg (i.e. 0.025mmol) Pd 2 (dba) 3 , 35mg (ie 0.15mmol) P (furyl) 3 , 2ml DMF. Then weigh 93mg (i.e. 1mmol) of aniline and 113mg (i.e. 1.1mmol) of tert-butyl nitrite in a long tube type reaction bottle, add 2ml of DMF, stir and inject into the Schlenk bottle with a needle, and the system is heated at 80°C React for 8 hours, concentrate after the reaction, and use petroleum ether as the eluent for column chromatography purification to obtain 4-methoxybiphenyl, whose structure is shown in the following formula:
[0031]
[0032] The compound is a white solid with a yield of 81%, and its NMR data are as follows:
[0033] 1 H NMR (400MHz, CDCl 3 )δ7.56~7.51(m, 4H), 7.43~7.39(m, 2H), 7.31~7.28(m, 1H), 6.99~6.96(m, 2H), 3.84(s, 3H); 13 C NMR (100MHz, CDCl 3 )δ 159.1, 140.8, 133.7, 128.7, 128.1, 126.7, 126.6, 114.2, 55.3.
Embodiment 2
[0035] Synthesis of 4-methyl 4'-methoxybiphenyl
[0036] Add 182mg (i.e. 1.2mmol) p-methoxyphenylboronic acid, 23mg (i.e. 0.025mmol) Pd 2 (dba) 3 , 35mg (ie 0.15mmol) P (furyl) 3 , 2ml DMF. Then take by weighing 107mg (i.e. 1mmol) p-toluidine and 113mg (i.e. 1.1mmol) tert-butyl nitrite in the long tube type reaction flask, add 2ml DMF, inject in the Schlenk bottle with needle after stirring, system is at 80 React at ℃ for 8 hours, concentrate after reaction, and use petroleum ether as eluent for column chromatography purification to obtain 4-methyl-4'-methoxybiphenyl, whose structure is shown in the following formula:
[0037]
[0038] The compound is a yellow solid with a yield of 77%, and its NMR data are as follows:
[0039] 1 H NMR (400MHz, CDCl 3 )δ7.50(d, 2H, J=8.8Hz), 7.44(d, 2H, J=8.1Hz), 7.22(d, 2H, J=7.9Hz), 6.96(d, 2H, J=8.8Hz) , 3.83(s, 3H), 2.34(s, 3H); 13 C NMR (100MHz, CDCl 3 ) 158.9, 137.9, 136.3, 133.7, 129.4, 127.9, 126.5, 114.1, 55.3, 21.0.
Embodiment 3
[0041] Synthesis of 4-Chloro4'-Methoxybiphenyl
[0042] Add 182mg (i.e. 1.2mmol) p-methoxyphenylboronic acid, 23mg (i.e. 0.025mmol) Pd 2 (dba) 3 , 35mg (ie 0.15mmol) P (furyl) 3 , 2ml DMF. Then take by weighing 128mg (i.e. 1mmol) p-chloroaniline and 113mg (i.e. 1.1mmol) tert-butyl nitrite in the long tube type reaction flask, add 2ml DMF, inject in the Schlenk bottle with needle after stirring, system is at 80 React at ℃ for 8 hours, concentrate after the reaction, and use petroleum ether as the eluent for column chromatography purification to obtain 4-chloro-4'-methoxybiphenyl, whose structure is shown in the following formula:
[0043]
[0044] The compound is a yellow solid with a yield of 75%, and its NMR data are as follows:
[0045] 1 H NMR (400MHz, CDCl 3 )δ7.48(d, 2H, J=6.3Hz), 7.46(d, 2H, J=6.1Hz), 7.37(d, 2H, J=8.7Hz), 6.97(d, 2H, J=8.9Hz) , 3.84(s, 3H); 13 C NMR (100MHz, CDCl 3 ) δ 159.3, 139.2, 132.6, 132.4, 128.8, 127.9, 127.9, 114.3, 55.3.
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