5-溴-1,2,4-三甲基苯合成路线 （共 32 条）
反应条件
1: lithium 2: titanium tetrachloride, zinc View Scheme
参考文献
Tetrahedron Letters, , vol. 28, # 30 p. 3479 - 3482
反应条件
diethyl ether; magnesium
参考文献
Smith; Kiess
Journal of the American Chemical Society, 1939 , vol. 61, p. 284,287
参考文献
Toehl; v. Karchowski
Chemische Berichte, 1892 , vol. 25, p. 1530
反应条件
1: 90.7 percent / conc. H2SO4, 98percent aq. HNO3 / CHCl3 / 2 h / 0 °C
2: 75.5 percent / NaOH, H2 / Raney Ni / ethanol / 114000 Torr
3: 1.) 25percent aq, H2SO4, aq. NaNO2, 2.) 20percent aq. H2SO4 / 1.) 0 deg C, 1 h, 2.) reflux, 2 h
4: 98 percent / NaH / dimethylsulfoxide / 10 h
5: 72 percent / phosphorus oxychloride / 24 h / 70 °C
6: 87 percent / 10percent aq. NaOH / 6 h / Ambient temperature
7: diethyl ether / 1.) 20 deg C, 2 h, 2.) reflux, 1 h
8: 1.) phosphorus oxychloride / 2.) a) 0 deg C, 0.5 h, b) 70 deg C, 2 h
View Scheme
参考文献
Makin, S. M.; Mikerin, I. E.; Dobretsova, E. K.; Shavrygina, O. A.
Russian Journal of Organic Chemistry, 1993 , vol. 29, # 4 p. 572 - 575
Zhurnal Organicheskoi Khimii, 1993 , vol. 29, # 4 p. 682 - 686
反应条件
1: concentrated H2SO4; chloroform; HNO3 / -5 - 0 °C
2: acetic acid; SnCl2; aqueous HCl / Erhitzen des erhaltenen 6-Brom-2.3.5-trimethyl-p-phenylendiamin-chlorostannats mit FeCl3 in wss. HCl
View Scheme
参考文献
Smith; Johnson
Journal of the American Chemical Society, 1937 , vol. 59, p. 673,678
反应条件
1: 90.7 percent / conc. H2SO4, 98percent aq. HNO3 / CHCl3 / 2 h / 0 °C
2: 75.5 percent / NaOH, H2 / Raney Ni / ethanol / 114000 Torr
View Scheme
参考文献
Makin, S. M.; Mikerin, I. E.; Dobretsova, E. K.; Shavrygina, O. A.
Russian Journal of Organic Chemistry, 1993 , vol. 29, # 4 p. 572 - 575
Zhurnal Organicheskoi Khimii, 1993 , vol. 29, # 4 p. 682 - 686
反应条件
1.1: 39 percent / PPh3; Et3N / Pd(OAc)2 / dimethylformamide
2.1: H2 / Pd black / ethanol
2.2: 88 percent / tetrapropylammonium perruthenate; NMO / CH2Cl2
3.1: 57 percent / LiHMDS / tetrahydrofuran
4.1: 100 percent / DIBAH / toluene
View Scheme
参考文献
Nakamura, Mitsuhiro; Mamino, Masashi; Masaki, Mizuki; Maki, Shojiro; Matsui, Ryo; Kojima, Satoshi; Hirano, Takashi; Ohmiya, Yoshihiro; Niwa, Haruki
Tetrahedron Letters, 2005 , vol. 46, # 1 p. 53 - 56
反应条件
1.1: 39 percent / PPh3; Et3N / Pd(OAc)2 / dimethylformamide
2.1: H2 / Pd black / ethanol
2.2: 88 percent / tetrapropylammonium perruthenate; NMO / CH2Cl2
3.1: 57 percent / LiHMDS / tetrahydrofuran
4.1: 100 percent / DIBAH / toluene
5.1: 70 percent / MnO2 / CH2Cl2
View Scheme
参考文献
Nakamura, Mitsuhiro; Mamino, Masashi; Masaki, Mizuki; Maki, Shojiro; Matsui, Ryo; Kojima, Satoshi; Hirano, Takashi; Ohmiya, Yoshihiro; Niwa, Haruki
Tetrahedron Letters, 2005 , vol. 46, # 1 p. 53 - 56
反应条件
chloroform; sulfuric acid; nitric acid
T=-5 - 0°C;
参考文献
Fittig
Justus Liebigs Annalen der Chemie, 1868 , vol. 147, p. 12
Full Text Show Details
Kelbe; Pathe
Chemische Berichte, 1886 , vol. 19, p. 1551
反应条件
1.1: 39 percent / PPh3; Et3N / Pd(OAc)2 / dimethylformamide
2.1: H2 / Pd black / ethanol
2.2: 88 percent / tetrapropylammonium perruthenate; NMO / CH2Cl2
View Scheme
参考文献
Nakamura, Mitsuhiro; Mamino, Masashi; Masaki, Mizuki; Maki, Shojiro; Matsui, Ryo; Kojima, Satoshi; Hirano, Takashi; Ohmiya, Yoshihiro; Niwa, Haruki
Tetrahedron Letters, 2005 , vol. 46, # 1 p. 53 - 56
