4-溴-1,2-亚甲二氧基苯合成路线 （共 128 条）
反应条件
1: 1) Mg, 1,2-dibromoethane / 1) THF, 0.5 h, 2) THF, 25 min
2: chromium trioxide, pyridine / CH2Cl2 / 0.33 h
3: 1) BuLi /hexane / 1) THF, -78 deg C, 20 min, 2) THF, r. t.
4: 1) Raney nickel, 2) H2, Pd/C / 1) 1,2-dimethoxyethane, ice-cooling, 2) acetic acid/water
View Scheme
参考文献
Rehnberg, Nicola; Magnusson, Goeran
Journal of Organic Chemistry, 1990 , vol. 55, # 14 p. 4340 - 4349
反应条件
n-butyllithium
1) in hexane, tetrahydrofuran, -78 deg C, 5 min 2) 0.5 h, -78 deg C, then -10 deg C; Yield given. Multistep reaction. Further byproducts given. Title compound not separated from byproducts;
参考文献
Sanghvi, Y. S.; Dabral, V.; Bhat, K. S.; Rao, A. S.
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1984 , vol. 23, # 1 p. 12 - 14
反应条件
n-butyllithium
1) in hexane, tetrahydrofuran, -78 deg C, 5 min 2) 0.5 h, -78 deg C, then -10 deg C; Multistep reaction. Further byproducts given. Title compound not separated from byproducts;
参考文献
Sanghvi, Y. S.; Dabral, V.; Bhat, K. S.; Rao, A. S.
Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1984 , vol. 23, # 1 p. 12 - 14
反应条件
tri-tert-butyl phosphine; sodium hydride; bis(dibenzylideneacetone)-palladium(0) in tetrahydrofuran
T=70°C; 6 h;
参考文献
Beare, Neil A.; Hartwig, John F.
Journal of Organic Chemistry, 2002 , vol. 67, # 2 p. 541 - 555
反应条件
triethylamine; palladium diacetate; triphenylphosphine
T=110°C; 8 h;
参考文献
Cutolo, M.; Fiandanese, V.; Naso, F.; Sciacovelli, O.
Tetrahedron Letters, 1983 , vol. 24, # 42 p. 4603 - 4606
反应条件
potassium hydroxide; tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide in benzene
12 h; Heating;
参考文献
Ishikura, Minoru; Oda, Izumi; Terashima, Masanao
Heterocycles, 1985 , vol. 23, # 9 p. 2375 - 2386
反应条件
1.1: n-BuLi / diethyl ether; hexane / 0.17 h / -30 °C
1.2: 80 percent / tetrahydrofuran; diethyl ether; hexane / 2 h / 20 °C
2.1: 97 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene; POCl3 / pyridine / 20 - 80 °C
3.1: H2 / Pd/C / methanol; tetrahydrofuran / 20 h
4.1: conc. sulfuric acid / tetrahydrofuran; H2O / 1.5 h
View Scheme
参考文献
Zhang, Xuqing; Hufnagel, Heather; Markotan, Thomas; Lanter, James; Cai, Chaozhong; Hou, Cuifen; Singer, Monica; Opas, Evan; McKenney, Sandra; Crysler, Carl; Johnson, Dana; Sui, Zhihua
Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 18 p. 5577 - 5582
反应条件
1.1: Mg / tetrahydrofuran
1.2: 81 percent / tetrahydrofuran / 1 h / 0 - 5 °C
2.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
2.2: 77 percent / tetrahydrofuran; hexane / -60 - 20 °C
3.1: SnCl4 / 1,2-dichloro-ethane / 2 h / 0 - 5 °C
4.1: 77 percent / N-bromosuccinimide; AIBN / benzene / 1 h / Heating
5.1: AcOH; K2CO3 / dimethylformamide / 2 h / 20 °C
5.2: 94 percent / KOH / dimethylformamide; methanol; H2O / 2 h / 20 °C
6.1: 86 percent / SmI2; HMPA / tetrahydrofuran / 2 h / 20 °C
7.1: 79 percent / Ag2CO3-Celite / benzene / 1.5 h / Heating
View Scheme
参考文献
Nishii, Yoshinori; Yoshida, Taichi; Asano, Hirofumi; Wakasugi, Kazunori; Morita, Jun-Ichi; Aso, Yoshifumi; Yoshida, Eri; Motoyoshiya, Jiro; Aoyama, Hiromu; Tanabe, Yoo
Journal of Organic Chemistry, 2005 , vol. 70, # 7 p. 2667 - 2678
反应条件
sodium carbonate; 1,2-bis-(diphenylphosphino)ethane; palladium diacetate in DMF (N,N-dimethyl-formamide)
T=110°C; Heck Reaction; 23 h;
参考文献
LYMPHOSIGN INC.
Patent: WO2005/777 A2, 2005 ;
Location in patent: Page 21; 22 ;
反应条件
1: 23.2 percent / ICI; AcOH / 18 h / 80 °C
2: 97 percent / neocuproine hydrate; CuI; NaO-t-Bu / dimethylformamide / 24 h / Heating
View Scheme
参考文献
He, Huazhong; Zatorska, Danuta; Kim, Joungnam; Aguirre, Julia; Llauger, Laura; She, Yuhong; Wu, Nian; Immormino, Robert M.; Gewirth, Daniel T.; Chiosis, Gabriela
Journal of Medicinal Chemistry, 2006 , vol. 49, # 1 p. 381 - 390
