(5-氯-2-碘苯基) 2,6-二氟苯甲烷合成路线 （共 11 条）
反应条件
1: With hydrogenchloride; acetic acid; sodium nitrite in water; ethyl acetate T=0 - 5°C; 0.833333 h; 2: With iodine; potassium iodide in water; ethyl acetate T=20°C; 1 h;
参考文献
Millennium Pharmaceuticals, Inc.
Patent: US2005/256102 A1, 2005 ;
Location in patent: Page/Page column 141 ;
US 20050256102 A1
反应条件
1.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C / Inert atmosphere 2.1: hydrogenchloride; acetic acid; sodium nitrite / water / 0 - 5 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere View Scheme
参考文献
Angewandte Chemie - International Edition, , vol. 51, # 27 p. 6598 - 6603
反应条件
1.1: tert.-butyl lithium / tetrahydrofuran; pentane / 3.33 h / -78 - -30 °C / Inert atmosphere 1.2: 0.83 h / -78 °C / Inert atmosphere 2.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C / Inert atmosphere 3.1: hydrogenchloride; acetic acid; sodium nitrite / water / 0 - 5 °C / Inert atmosphere 3.2: 0 - 20 °C / Inert atmosphere View Scheme
参考文献
Angewandte Chemie - International Edition, , vol. 51, # 27 p. 6598 - 6603
反应条件
1.1: tert.-butyl lithium / tetrahydrofuran; pentane / 3.33 h / -78 - -30 °C / Inert atmosphere 1.2: 0.83 h / -78 °C / Inert atmosphere 2.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C / Inert atmosphere 3.1: hydrogenchloride; acetic acid; sodium nitrite / water / 0 - 5 °C / Inert atmosphere 3.2: 0 - 20 °C / Inert atmosphere View Scheme
参考文献
Angewandte Chemie - International Edition, , vol. 51, # 27 p. 6598 - 6603
反应条件
1.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / dichloromethane / 0.5 h / Inert atmosphere 1.2: 16 h / 20 °C / Inert atmosphere 2.1: sulfuric acid / dichloromethane / 0 °C / Inert atmosphere 3.1: toluene / 4 h / 80 °C / Inert atmosphere 4.1: potassium carbonate / ethanol / 14 h / Inert atmosphere; Reflux View Scheme
参考文献
Yang, Katherine S.; Budin, Ghyslain; Reiner, Thomas; Vinegoni, Claudio; Weissleder, Ralph
Angewandte Chemie - International Edition, 2012 , vol. 51, # 27 p. 6598 - 6603
反应条件
1.1: tert-butyl methyl ether; methanol / 3.5 h / 25 - 30 °C 2.1: diethylamine; copper(l) iodide / bis-triphenylphosphine-palladium(II) chloride / cyclohexane / 15 h / 28 - 33 °C / Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane; water / 20 h / 20 - 35 °C 3.2: 2.5 h / 20 - 30 °C / pH 8 3.3: 20.5 h / 20 - 42 °C 4.1: potassium carbonate / methanol / 24 h / 50 - 55 °C 4.2: 2 h / 20 - 55 °C / pH 3 View Scheme
参考文献
MILLENNIUM PHARMACEUTICALS, INC.; ARMITAGE, Ian; COOPER, Martin, I.; EDDLESTON, Mark, D.; FAIBER, Neil, C.; MCCUBBIN, Quentin, J.; WATT, Stephen, W.
Patent: WO2011/103089 A1, 2011 ;
WO 2011/103089 A1
反应条件
in methanol; tert-butyl methyl ether T=25 - 30°C; 3.5 h;
参考文献
MILLENNIUM PHARMACEUTICALS, INC.; ARMITAGE, Ian; COOPER, Martin, I.; EDDLESTON, Mark, D.; FAIBER, Neil, C.; MCCUBBIN, Quentin, J.; WATT, Stephen, W.
Patent: WO2011/103089 A1, 2011 ;
Location in patent: Page/Page column 40-41 ;
WO 2011/103089 A1
反应条件
1: With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide in dichloromethane
0.5 h;
2: With diethylamine in dichloromethane
T=20°C; 16 h;
参考文献
Millennium Pharmaceuticals, Inc.
Patent: US2005/256102 A1, 2005 ;
Location in patent: Page/Page column 142-143 ;
US 20050256102 A1
反应条件
1.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / dichloromethane / 0.5 h / Inert atmosphere
1.2: 16 h / 20 °C / Inert atmosphere
2.1: sulfuric acid / dichloromethane / 0 °C / Inert atmosphere
View Scheme
参考文献
Yang, Katherine S.; Budin, Ghyslain; Reiner, Thomas; Vinegoni, Claudio; Weissleder, Ralph
Angewandte Chemie - International Edition, 2012 , vol. 51, # 27 p. 6598 - 6603
反应条件
1: tert-butyl methyl ether; methanol / 3.5 h / 25 - 30 °C
2: diethylamine; copper(l) iodide / bis-triphenylphosphine-palladium(II) chloride / cyclohexane / 15 h / 28 - 33 °C / Inert atmosphere
View Scheme
参考文献
MILLENNIUM PHARMACEUTICALS, INC.; ARMITAGE, Ian; COOPER, Martin, I.; EDDLESTON, Mark, D.; FAIBER, Neil, C.; MCCUBBIN, Quentin, J.; WATT, Stephen, W.
Patent: WO2011/103089 A1, 2011 ;
WO 2011/103089 A1
