4-(叔丁基二甲基硅氧基)苯基硼酸合成路线 （共 10 条）
反应条件
1: With n-butyllithium in tetrahydrofuran; hexane T=-78°C; Metallation; 1 h; 2: With tri-isopropoxy-borane in tetrahydrofuran; hexane T=-78 - 0°C; Metallation; 3: With hydrogenchloride in tetrahydrofuran; hexane; water Hydrolysis;
参考文献
Hajduk; Sheppard; Nettesheim; Olejniczak; Shuker; Meadows; Steinman; Carrera Jr.; Marcotte; Severin; Walter; Smith; Gubbins; Simmer; Holzman; Morgan; Davidsen; Summers; Fesik
Journal of the American Chemical Society, 1997 , vol. 119, # 25 p. 5818 - 5827
反应条件
1H-imidazole in N,N-dimethyl-formamide T=20°C;
参考文献
CHUGAI SEIYAKU KABUSHIKI KAISHA
Patent: US2011/275703 A1, 2011 ;
Location in patent: Page/Page column 35 ;
反应条件
1: 1-bromo-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzene With n-butyllithium in tetrahydrofuran T=-78°C; 0.5 h; 2: tri-isopropoxy-borane in tetrahydrofuran T=-78 - 20°C; Further stages.;
参考文献
Bursavich; West; Rich
Organic letters, 2001 , vol. 3, # 15 p. 2317 - 2320
反应条件
1.1: 99 percent / imidazole / CH2Cl2 / 0.17 h 2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: triisopropyl borate / tetrahydrofuran; hexane / -78 - 0 °C 2.3: 97 percent / HCl / tetrahydrofuran; hexane; H2O View Scheme
参考文献
Journal of the American Chemical Society, , vol. 119, # 25 p. 5818 - 5827
反应条件
1: 1-bromo-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzene With n-butyllithium in tetrahydrofuran T=-75°C; 1 h; Inert atmosphere; 2: boric acid trimethyl ester in tetrahydrofuran T=-65 - 20°C; 16 h; Inert atmosphere; 3: With hydrogenchloride in tetrahydrofuran pH=6 - 7;
参考文献
Sunden, Henrik; Ma, Jian-Nong; Hansen, Lars K.; Gustavsson, Anna-Lena; Burstein, Ethan S.; Olsson, Roger
ChemMedChem, 2013 , vol. 8, # 8 p. 1283 - 1294
反应条件
1.1: 99 percent / imidazole / CH2Cl2 / 0.17 h 2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: triisopropyl borate / tetrahydrofuran; hexane / -78 - 0 °C 2.3: 97 percent / HCl / tetrahydrofuran; hexane; H2O View Scheme
参考文献
Journal of the American Chemical Society, , vol. 119, # 25 p. 5818 - 5827
反应条件
1: 128 mg / Na2CO3 / Pd(PPH3)4 / toluene; H2O / 2 h / 85 °C 2: tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h View Scheme
参考文献
Hajduk; Sheppard; Nettesheim; Olejniczak; Shuker; Meadows; Steinman; Carrera Jr.; Marcotte; Severin; Walter; Smith; Gubbins; Simmer; Holzman; Morgan; Davidsen; Summers; Fesik
Journal of the American Chemical Society, 1997 , vol. 119, # 25 p. 5818 - 5827
反应条件
1: 48 percent / sodium carbonate / tetrakis(triphenylphosphine)palladium / 1,2-dimethoxy-ethane; H2O / 3.5 h / Heating 2: KF; aqueous HBr / dimethylformamide / 2.5 h / 20 °C View Scheme
参考文献
Bioorganic and Medicinal Chemistry, , vol. 12, # 10 p. 2553 - 2570
反应条件
1: 52 percent / Na2CO3; LiCl / Pd(PPh3)4 / 1,2-dimethoxy-ethane; H2O / 2 h / Heating
2: 92 percent / AD-mix-α; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 0 - 20 °C
3: TBAF / tetrahydrofuran / 0 - 20 °C
4: 1.10 g / Raney Ni / ethanol / 4 h / Heating
View Scheme
参考文献
Bursavich; West; Rich
Organic letters, 2001 , vol. 3, # 15 p. 2317 - 2320
反应条件
1: With anhydrous copper acetate in methanol
T=28°C; 6 h; Inert atmosphere;
2: With hydrogenchloride in methanol
6 h; Inert atmosphereReflux;
参考文献
Yamamoto, Yoshihiko; Kirai, Naohiro
Organic Letters, 2008 , vol. 10, # 24 p. 5513 - 5516
