5-溴-3, 4-二羟苯甲醛合成路线 (共 23 条)
反应条件
1: 86 percent / potassium carbonate / dimethylformamide / 3 h / Heating 2: 91 percent / ammonium chloride / methanol / 4 h / Heating 3: 94 percent / 1.) n-butyl lithium / hexane; diethyl ether / 1.) -78 deg C, 10 min, 2.) -78 deg C to room temperature, 3 h 4: 93 percent / potassium hydroxide / ethanol / 4 h 5: 87 percent / conc. HCl / dioxane; methanol / 1.5 h / Ambient temperature 6: 92 percent / 30percent H2O2, 5percent NaOH / dioxane; methanol / 3 h / Ambient temperature 7: 1.) boron trifluoride etherate, 2.) sodium borohydride / 1.) benzene, 20 min, 2.) THF, room temperature, 2 h 8: 66 percent / hydrogen / 10percent Pd/C / methanol 9: 77 percent / boron trifluoride etherate / acetic acid / 0.25 h / 5 °C 10: 66 percent / diisopropylethylamine / CH2Cl2 / 3 h / Ambient temperature 11: 91 percent / 1N NaOH / methanol / 1 h / Ambient temperature 12: 95 percent / manganese dioxide / CH2Cl2 / 0.5 h 13: 94 percent / sodium hydroxide / ethanol / 4 h 14: 96 percent / 30percent H2O2, 5percent NaOH / methanol / 4 h / Ambient temperature 15: 19 percent / conc. HCl / methanol / 0.25 h / 70 °C View Scheme
参考文献
Tanaka; Hiroo; Ichino; Ito
Chemical and Pharmaceutical Bulletin, 1989 , vol. 37, # 6 p. 1441 - 1445
反应条件
KF in N,N-dimethyl-formamide
参考文献
Pfahl, Magnus; Tachdjian, Catherine; Al-Shamma, Hussien A.; Fanjul, Andrea; Pleynet, David P.M.; Spruce, Lyle W.; Wiemann, Torsten R.; Ibarra, Jason B.
Patent: US2002/143182 A1, 2002 ;
反应条件
potassium fluoride in N,N-dimethyl-formamide T=105°C; 2 h;
参考文献
Walz; Sundberg
Journal of Organic Chemistry, 2000 , vol. 65, # 23 p. 8001 - 8010
反应条件
caesium carbonate in DMF (N,N-dimethyl-formamide) T=110°C; 20 h;
参考文献
EISAI CO. LTD.
Patent: WO2003/76424 A1, 2003 ;
Location in patent: Page/Page column 218-219 ;
反应条件
potassium carbonate in N,N-dimethyl-formamide T=100°C; 3 h;
参考文献
Shaikh, Ajam C.; Wang, Yu-Yun; Chen, Chinpiao
Journal of Labelled Compounds and Radiopharmaceuticals, 2007 , vol. 50, # 7 p. 660 - 665
反应条件
potassium hydroxide; dimethyl sulfate
参考文献
Erne; Ramirez
Helvetica Chimica Acta, 1950 , vol. 33, p. 912,915
Full Text Show Details
Kondo et al.
Itsuu Kenkyusho Nempo, 1950 , # 1 p. 15,16; engl. Ref. S. 54, 55
Chem.Abstr., 1953 , p. 7518
参考文献
Pschorr
Justus Liebigs Annalen der Chemie, 1912 , vol. 391, p. 44
反应条件
1: aqueous KOH-solution; methylene sulfate 2: acetone; aqueous potassium permanganate solution View Scheme
参考文献
Kondo et al.
Itsuu Kenkyusho Nempo, 1950 , # 1 p. 15,16; engl. Ref. S. 54, 55
Chem.Abstr., 1953 , p. 7518
反应条件
1.1: 71 percent / copper(II) chloride / dimethylformamide / 2 h / Heating 2.1: pyridine / 55 °C 2.2: 94 percent / aniline; piperidine / 20 °C View Scheme
参考文献
Russell, Wendy R.; Burkitt, Mark J.; Scobbie, Lorraine; Chesson, Andrew
Bioorganic Chemistry, 2003 , vol. 31, # 3 p. 206 - 215
反应条件
1.1: 63 percent / K2CO3 / dimethylformamide / 3 h / 100 °C
2.1: toluene / 3.5 h / Heating
3.1: n-BuLi / diethyl ether; hexane / -78 °C
3.2: diethyl ether; hexane / -78 - 20 °C
4.1: H2O2 / methanol; H2O / 0.25 h
4.2: 0.91 g / aq. HCl / 100 °C
View Scheme
参考文献
Sinhababu, Achintya K.; Borchardt, Ronald T.
Journal of Organic Chemistry, 1983 , vol. 48, # 12 p. 1941 - 1944