2-溴-5-甲氧基苯甲酸合成路线 （共 95 条）
反应条件
1: methanol. potassium ethylate; isoamyl alcohol; copper (I)-chloride / weiteres Reagens: Kupfer
2: chlorobenzene; phosphoryl chloride
3: 4-amino-1-diethylamino-pentane
View Scheme
参考文献
Dauben
Journal of the American Chemical Society, 1948 , vol. 70, p. 2420,2422
反应条件
Multistep reaction. Title compound not separated from byproducts;
参考文献
Cipollina, Joseph A.; Ruediger, Edward H.; New, James S.; Wire, Mary E.; Shepherd, Timothy A.; et al.
Journal of Medicinal Chemistry, 1991 , vol. 34, # 11 p. 3316 - 3328
反应条件
1: With 1,1'-carbonyldiimidazole in N,N-dimethyl-formamide
T=20°C; 0.5 h;
2: With (NH4)2CO3 in N,N-dimethyl-formamide
参考文献
Millennium Pharmaceuticals, Inc.
Patent: US2008/171754 A1, 2008 ;
Location in patent: Page/Page column 105 ;
US 20080171754 A1
反应条件
1: 84 percent / sodium carbonate / tris(dibenzylideneacetone)dipalladium(0) / 1,2-dimethoxy-ethane; H2O / 16 h / 85 °C
2: 88 percent / sodium hydroxide / ethanol / 78 °C
View Scheme
参考文献
Epperson, James R.; Bruce, Marc A.; Catt, John D.; Deskus, Jeffrey A.; Hodges, Donald B.; Karageorge, George N.; Keavy, Daniel J.; Mahle, Cathy D.; Mattson, Ronald J.; Ortiz, Astrid A.; Parker, Michael F.; Takaki, Katherine S.; Watson, Brett T.; Yevich, Joseph P.
Bioorganic and Medicinal Chemistry, 2004 , vol. 12, # 17 p. 4601 - 4611
反应条件
1: 2-bromo-5-methoxy benzoic acid With n-butyllithium in tetrahydrofuran
T=-78°C;
2: N,N-dimethyl-formamide in tetrahydrofuran
2 h;
3: With hydrogenchloride in water; N,N-dimethyl-formamide
参考文献
BOEHRINGER INGELHEIM INTERNATIONAL GMBH; CHEN, Zhidong; DE LOMBAERT, Stephane; DINES, Jonathon, Alan; LIU, Weimin; LO, Ho Yin; LOKE, Pui Leng
Patent: WO2012/58254 A1, 2012 ;
Location in patent: Page/Page column 50 ;
WO 2012/058254 A1
反应条件
2: SOCl2, DMF / CHCl3 / Heating
3: CH2Cl2 / 18 h / Ambient temperature
View Scheme
参考文献
Cipollina, Joseph A.; Ruediger, Edward H.; New, James S.; Wire, Mary E.; Shepherd, Timothy A.; et al.
Journal of Medicinal Chemistry, 1991 , vol. 34, # 11 p. 3316 - 3328
反应条件
copper(I) bromide; sodium hydride
参考文献
Weimar; Van Angerer; Wiegrebe
Archiv der Pharmazie, 1991 , vol. 324, # 8 p. 509 - 518
反应条件
1: sodium; copper(I) bromide / 12 h / 70 °C
2: water; lithium hydroxide hydrate / methanol / 12 h / 40 °C
3: toluene / 12 h / 105 °C
View Scheme
参考文献
AbbVie Inc.; Abbott GmbH and Co. KG; Geneste, Hervé; Ochse, Michael; Drescher, Karla; Dinges, Jürgen; Jakob, Clarissa
Patent: US2013/116229 A1, 2013 ;
反应条件
1.1: 99 percent / H2SO4 / 3 h / Heating
2.1: 57 percent / Pd(PPh3)4 / benzene / 20 h / 120 °C
3.1: 79 percent / NaOH / H2O; ethanol / 1 h / Heating
4.1: diethyl cyanophosphonate / dimethylformamide / 0.5 h / 0 °C
4.2: Et3N / dimethylformamide / 2 h / 0 °C
5.1: 63 percent / 1,4,8,11-tetraazacyclotetradecane based Ni(II) complex; tetraethylammonium tosylate / dimethylformamide / 60 °C / Electrolysis
View Scheme
参考文献
Ozaki, Shigeko; Adachi, Masashi; Sekiya, Sayaka; Kamikawa, Rie
Journal of Organic Chemistry, 2003 , vol. 68, # 11 p. 4586 - 4589
反应条件
1: thionyl chloride
2: CH2Cl2
View Scheme
参考文献
Tang, Xiubo; Zhang, Dongheng; Jie, Suyun; Sun, Wen-Hua; Chen, Jiutong
Journal of Organometallic Chemistry, 2005 , vol. 690, # 17 p. 3918 - 3928
