6-溴-3,4-亚甲基二氧苯甲醛合成路线 （共 110 条）
反应条件
1: 91 percent / TsOH / ethanol / 2 h / Heating
2: 1.) 15 percent BuLi / 1.) ether, hexane, 0 deg C, 3 h, 2.) -50 deg C, 30 min; room temp., 1 h
3: 92 percent / 85 percent H3PO4 / dioxane; H2O / 12 h / Ambient temperature
4: 20 percent / Triton B / methanol / 16 h / Heating
View Scheme
参考文献
Dallacker, Franz; Schleuter, Hans-Joachim; Schneider, Petra
Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1986 , vol. 41, # 10 p. 1273 - 1280
反应条件
1: p-TsOH / benzene / 15 h / Heating
2: n-BuLi, I2 / hexane; tetrahydrofuran
3: 20percent aq. HCl / methanol; benzene / 16 h
4: 97 percent / NaBH4 / propan-2-ol / 16 h / Heating
View Scheme
参考文献
Bogucki; Charlton
Journal of Organic Chemistry, 1995 , vol. 60, # 3 p. 588 - 593
反应条件
1: (iodo-2 trimethoxy-3,4,5 benzyl)-3-butanolide-4, Copper bronze / 0.58 h / 225 °C
2: 69.5 percent / Na / methanol / 1.33 h / Heating
View Scheme
参考文献
Brown, Eric; Robin, Jean-Pierre; Dhal, Robert
Tetrahedron, 1982 , vol. 38, # 16 p. 2569 - 2580
反应条件
1: copper-powder / 250 °C
2: acetone; aqueous potassium permanganate solution
3: quinoline; copper oxide-chromium oxide
View Scheme
参考文献
Uyeo
Chemische Berichte, 1940 , vol. 73, p. 661,665
反应条件
copper in N,N-dimethyl-formamide
T=165°C; Ullmann Reaction; 3 h;
参考文献
THE UNIVERSITY OF MANCHESTER
Patent: WO2008/75048 A2, 2008 ;
Location in patent: Page/Page column 68 ;
反应条件
copper in N,N-dimethyl-formamide
T=165°C; Ullmann reaction; 3 h;
参考文献
Edwards, David J.; Hadfield, John A.; Wallace, Timothy W.; Ducki, Sylvie
Organic and Biomolecular Chemistry, 2011 , vol. 9, # 1 p. 219 - 231
反应条件
1: 92 percent / concd. HNO3 / 0 °C
2: 96 percent / concd. HCl, acetic acid, Zn / 0.25 h / 0 °C
3: 90 percent / concd. HCl / ethanol
4: 1.) aq. HCl, sodium nitrite, 2.) 48percent aq. HBF4 / 1.) 0 deg C, 5 min, 2.) 0 deg C, 30 min
5: 13 percent / 48percent aq. HBF4 / 1 h / Irradiation
View Scheme
参考文献
Jung, Michael E.; Lam, Patrick Yuk-Sun; Mansuri, Muzzamil M.; Speltz, Laurine M.
Journal of Organic Chemistry, 1985 , vol. 50, # 7 p. 1087 - 1105
反应条件
1: 92 percent / concd. HNO3 / 0 °C
2: 96 percent / concd. HCl, acetic acid, Zn / 0.25 h / 0 °C
3: 90 percent / concd. HCl / ethanol
4: 1.) aq. HCl, sodium nitrite, 2.) aq. KI / 1.) 0 deg C, 10 min
View Scheme
参考文献
Jung, Michael E.; Lam, Patrick Yuk-Sun; Mansuri, Muzzamil M.; Speltz, Laurine M.
Journal of Organic Chemistry, 1985 , vol. 50, # 7 p. 1087 - 1105
反应条件
1: 92 percent / concd. HNO3 / 0 °C
2: 96 percent / concd. HCl, acetic acid, Zn / 0.25 h / 0 °C
3: 90 percent / concd. HCl / ethanol
4: 1.) aq. HCl, sodium nitrite, 2.) aq. KI / 1.) 0 deg C, 10 min
5: 88 percent / Mg/CH3I / tetrahydrofuran / 21 h / Heating
View Scheme
参考文献
Jung, Michael E.; Lam, Patrick Yuk-Sun; Mansuri, Muzzamil M.; Speltz, Laurine M.
Journal of Organic Chemistry, 1985 , vol. 50, # 7 p. 1087 - 1105
反应条件
1: TsOH / toluene / Heating
2: 1.) n-BuLi / 1.) -60 deg C, ether
3: KOt-Bu / tetrahydrofuran
4: aq. HCl, CH2Cl2
5: 66 percent / NaOMe, MeOH / tetrahydrofuran / 5 °C
6: 55 percent / xylene / Heating
7: 80 percent / sodium cyanoborohydride / acetic acid
8: 70 percent / DIBAL / toluene / -70 °C
9: 51 percent / Ph2P(CH3)2PPh2 / (Ph3P)Rh(CO)Cl / xylene / Heating
View Scheme
参考文献
Moody, Christopher J.; Warrellow, Graham J.
Tetrahedron Letters, 1987 , vol. 28, # 48 p. 6089 - 6092
