5-溴-6-溴甲基-1,3-苯并二氧杂环戊二烯合成路线 （共 21 条）
反应条件
1: acetic acid 2: sodium methylate; methanol View Scheme
参考文献
Barthel; Alexander
Journal of Organic Chemistry, 1958 , vol. 23, p. 1012
反应条件
bromine in chloroform
T=60°C; Bromination; 6 h;
参考文献
Olivera, Roberto; SanMartin, Raul; Dominguez, Esther; Solans, Xabier; Urtiaga, Miren Karmele; Arriortua, Maria Isabel
Journal of Organic Chemistry, 2000 , vol. 65, # 20 p. 6398 - 6411
反应条件
bromine
T=60°C; 12 h;
参考文献
3-DIMENSIONAL PHARMACEUTICALS, INC.
Patent: WO2003/99805 A1, 2003 ;
Location in patent: Page 418-419 ;
反应条件
phosphorus tribromide in diethyl ether; benzene
1 h; Heating;
参考文献
Mervic, Miljenko; Ghera, Eugene
Journal of Organic Chemistry, 1980 , vol. 45, # 23 p. 4720 - 4725
反应条件
N-bromosuccinmide; dibenzoyl peroxide in tetrachloromethane
T=70°C; 18 h;
参考文献
Kukosha, Tatyana; Trufilkina, Nadezhda; Katkevics, Martins
Synlett, 2011 , # 17 p. 2525 - 2528
反应条件
n-butyllithium; N,N,N',N,-tetramethylethylenediamine; tert.-butyl lithium
1.) THF, -30 deg C, 2 h, 2.) THF, -78 deg C - RT, 3 h; Yield given. Multistep reaction. Yields of byproduct given;
参考文献
Cavicchioli, Marcello; Decortiat, Sylvie; Bouyssi, Didier; Gore, Jacques; Balme, Genevieve
Tetrahedron, 1996 , vol. 52, # 35 p. 11463 - 11478
反应条件
1: aq. NaOH solution
2: water; hydrobromic acid
View Scheme
参考文献
Naik; Wheeler
Journal of the Chemical Society, 1938 , p. 1780,1782
反应条件
1.1: BuLi / tetrahydrofuran / -50 - 20 °C
1.2: 78 percent / tetrahydrofuran / 0.25 h / -50 °C
2.1: tBuLi / tetrahydrofuran / -110 - 20 °C
2.2: MeOH / tetrahydrofuran / -78 - 20 °C
3.1: DIBAL-H; [NiCl2(dppp)] / toluene / 2 h / 20 °C
4.1: 0.214 g / PCC / CH2Cl2 / 2 h / Heating
View Scheme
参考文献
Sanz, Roberto; Fernandez, Yolanda; Castroviejo, M. Pilar; Perez, Antonio; Fananas, Francisco J.
European Journal of Organic Chemistry, 2007 , # 1 p. 62 - 69
反应条件
1: potassium iodide / acetonitrile / 0.25 h / 170 °C / |Sealed tube; |Microwave irradiation; |Inert atmosphere
2: acetonitrile / 2 h / |Inert atmosphere; |Photolysis
View Scheme
参考文献
Linsenmeier, Anna M.; Williams, Craig M.; Braese, Stefan
European Journal of Organic Chemistry, 2013 , # 18 p. 3847 - 3856
反应条件
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.08 h / 0 °C / |Inert atmosphere
1.2: 2 h / 0 - 20 °C / |Inert atmosphere
2.1: 1,10-phenanthroline; potassium tert-butylate / 1,3,5-trimethyl-benzene / 20 h / 110 °C / |Inert atmosphere; |Schlenk technique; |Sealed tube
View Scheme
参考文献
De, Subhadip; Mishra, Sourabh; Kakde, Badrinath N.; Dey, Dhananjay; Bisai, Alakesh
Journal of Organic Chemistry, 2013 , vol. 78, # 16 p. 7823 - 7844
