1-溴-3-甲氧基-5-甲苯合成路线 （共 31 条）
反应条件
1: 50 percent / aq. KMnO4; pyridine / 24 h / 75 °C 2: 81 percent / LiAlH4 / diethyl ether / 3 h / 20 °C 3: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2 h View Scheme
参考文献
Claudi, Francesco; Di Stefano, Antonio; Napolitani, Fabrizio; Cingolani, Gian Mario; Giorgioni, Gianfabio; Fontenla, Jose A.; Montenegro, Gisela Y.; Rivas, Maria E.; Rosa, Elizabeth; Michelotto, Barbara; Orlando, Giustino; Brunetti, Luigi
Journal of Medicinal Chemistry, 2000 , vol. 43, # 4 p. 599 - 608
反应条件
1: 5-bromo-3-methoxytoluene With n-butyllithium in tetrahydrofuran; hexane
T=-78°C; 0.5 h;
2: boric acid trimethyl ester in tetrahydrofuran; hexane
T=-78 - 20°C; 1.5 h;
3: With hydrogenchloride; water
more than 3 stages;
参考文献
SMITHKLINE BEECHAM CORPORATION; VITAE PHARMACEUTICALS, INC.
Patent: WO2008/124575 A1, 2008 ;
Location in patent: Page/Page column 128-139 ;
WO 2008/124575 A1
反应条件
1: 5-bromo-3-methoxytoluene With n-butyllithium in tetrahydrofuran; hexane
T=-78°C; 0.5 h;
2: boric acid trimethyl ester in tetrahydrofuran; hexane
T=-78 - 20°C; 1.5 h;
3: hydrogenchloride; water in tetrahydrofuran; hexane
pH=3; Cooling;
参考文献
SMITHKLINE BEECHAM CORPORATION; VITAE PHARMACEUTICALS, INC.
Patent: WO2008/124582 A1, 2008 ;
Location in patent: Page/Page column 118-119 ;
WO 2008/124582 A1
反应条件
1.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C
1.2: tetrahydrofuran; hexane / -78 - 20 °C
2.1: 1.494 g / aq. HCl / tetrahydrofuran / 2 h / 20 °C
View Scheme
参考文献
Trost, Barry M.; Pissot-Soldermann, Carole; Chen, Irwin
Chemistry - A European Journal, 2005 , vol. 11, # 3 p. 951 - 959
反应条件
1: 16 percent / copper(II) nitrate trihydrate, acetic anhydride / 1.5 h / 30 °C
2: 75 percent / potassium carbonate, copper(II) oxide / 16 h / 140 °C
3: 90 percent / bromine / CH2Cl2 / 0.25 h
4: 69 percent / tin(II) chloride dihydrate, hydrochloric acid / methanol / 4 h / Heating
5: 1.) isopentyl nitrite, 2.) copper(II) bromide / 1.) acetonitrile
6: 48 percent / copper bronze / 2 h / 260 °C
7: 98 percent / potassium hydroxide, water / dimethylsulfoxide / 1.67 h / Heating
8: 11 percent / copper chromite / quinoline / 1.5 h / 180 °C
View Scheme
参考文献
Carvalho, Christopher F.; Sargent, Melvyn V.
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984 , # 7 p. 1613 - 1620
参考文献
Dubinin
Zhurnal Obshchei Khimii, 1937 , vol. 7, p. 2183,2187
Chem. Zentralbl., 1938 , vol. 109, # I p. 3909
反应条件
1: 26 percent / copper(II) nitrate trihydrate, acetic anhydride / 1.5 h / 30 °C
2: 1.) hydrogen / 1.) palladized charcoal / 1.) ethanol, 18 h
View Scheme
参考文献
Carvalho, Christopher F.; Sargent, Melvyn V.
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984 , # 7 p. 1613 - 1620
反应条件
n-butyllithium in tetrahydrofuran
T=-70°C; 2 h;
参考文献
BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BRENNEMAN, Jehrod Burnett; GINN, John; LOWE, Michael D.; SARKO, Christopher Ronald; TASBER, Edward S.; ZHANG, Zhonghua
Patent: US2014/73629 A1, 2014 ;
Location in patent: Paragraph 0262 ;
反应条件
copper (I) cyanide in DMF (N,N-dimethyl-formamide)
T=60°C; 20 h;
参考文献
BIOVITRUM AB
Patent: WO2004/63156 A1, 2004 ;
Location in patent: Page 30-31 ;
WO 2004/063156 A1
反应条件
tetrakis(triphenylphosphine) palladium(0) in N,N-dimethyl-formamide
T=90°C; 7 h;
参考文献
GILEAD SCIENCES, INC.; KOREAN RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY
Patent: WO2009/5674 A2, 2009 ;
Location in patent: Page/Page column 423 ;
