2-(3-溴-4-羟基苯基)乙酸甲酯合成路线 （共 20 条）
反应条件
1.1: potassium carbonate / acetone / |Reflux 2.1: potassium hydroxide; water; copper; copper(II) oxide / 1 h / 140 °C / |Inert atmosphere; |Microwave irradiation 3.1: 3,4,5-trimethoxyphenylboronic acid / toluene / 1 h / |Reflux; |Dean-Stark 3.2: 46 h / 100 °C / |Molecular sieve; |Sealed tube 3.3: 2 h / |Reflux 4.1: potassium carbonate / acetone / 4 h / |Reflux 5.1: ethanol / 14 h / |Reflux 6.1: pyridine / dichloromethane / 1.5 h / 0 - 20 °C 7.1: trichlorophosphate / acetonitrile / 1 h / |Reflux; |Inert atmosphere 8.1: [[(η6-p-cymene)((1S,2S)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine)]Ru]; formic acid; triethylamine / N,N-dimethyl-formamide / 20 °C 9.1: water; sodium hydroxide / ethanol / 3 h / 20 °C 10.1: thionyl chloride / dichloromethane / 1.5 h / 0 - 20 °C 11.1: sodium hydrogencarbonate / dichloromethane / 1.5 h / 20 °C 12.1: hydrogenchloride / water; ethanol / 2 h / |Reflux View Scheme
参考文献
Sun, Haifeng; Zhu, Liyuan; Yang, Huicui; Qian, Wangke; Guo, Lin; Zhou, Shengbin; Gao, Bo; Li, Zeng; Zhou, Yu; Jiang, Hualiang; Chen, Kaixian; Zhen, Xuechu; Liu, Hong
Bioorganic and Medicinal Chemistry, 2013 , vol. 21, # 4 p. 856 - 868
反应条件
1: aq. NaOH solution 2: ethanolic KOH-solution View Scheme
参考文献
Kondo; Uyeo
Yakugaku Zasshi, 1933 , vol. 53, p. 557,563; dtsch. Ref. S. 92
Chem.Abstr., 1933 , p. 4223
参考文献
Kondo et al.
Itsuu Kenkyusho Nempo, 1958 , # 9 p. 1,4; engl. Ref. S. 59, 62
Chem.Abstr., 1960 , p. 1399
反应条件
1: potassium carbonate / acetone / |Reflux 2: potassium hydroxide; water; copper; copper(II) oxide / 1 h / 140 °C / |Inert atmosphere; |Microwave irradiation View Scheme
参考文献
Sun, Haifeng; Zhu, Liyuan; Yang, Huicui; Qian, Wangke; Guo, Lin; Zhou, Shengbin; Gao, Bo; Li, Zeng; Zhou, Yu; Jiang, Hualiang; Chen, Kaixian; Zhen, Xuechu; Liu, Hong
Bioorganic and Medicinal Chemistry, 2013 , vol. 21, # 4 p. 856 - 868
反应条件
1.1: potassium carbonate / acetone / |Reflux 2.1: potassium hydroxide; water; copper; copper(II) oxide / 1 h / 140 °C / |Inert atmosphere; |Microwave irradiation 3.1: 3,4,5-trimethoxyphenylboronic acid / toluene / 1 h / |Reflux; |Dean-Stark 3.2: 46 h / 100 °C / |Molecular sieve; |Sealed tube 3.3: 2 h / |Reflux 4.1: potassium carbonate / acetone / 4 h / |Reflux 5.1: ethanol / 14 h / |Reflux 6.1: pyridine / dichloromethane / 1.5 h / 0 - 20 °C 7.1: trichlorophosphate / acetonitrile / 1 h / |Reflux; |Inert atmosphere 8.1: [[(η6-p-cymene)((1S,2S)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine)]Ru]; formic acid; triethylamine / N,N-dimethyl-formamide / 20 °C 9.1: water; sodium hydroxide / ethanol / 3 h / 20 °C 10.1: thionyl chloride / dichloromethane / 1.5 h / 0 - 20 °C 11.1: sodium hydrogencarbonate / dichloromethane / 1.5 h / 20 °C 12.1: hydrogenchloride / water; ethanol / 2 h / |Reflux View Scheme
参考文献
Sun, Haifeng; Zhu, Liyuan; Yang, Huicui; Qian, Wangke; Guo, Lin; Zhou, Shengbin; Gao, Bo; Li, Zeng; Zhou, Yu; Jiang, Hualiang; Chen, Kaixian; Zhen, Xuechu; Liu, Hong
Bioorganic and Medicinal Chemistry, 2013 , vol. 21, # 4 p. 856 - 868
反应条件
1.1: potassium carbonate / acetone / |Reflux 2.1: potassium hydroxide; water; copper; copper(II) oxide / 1 h / 140 °C / |Inert atmosphere; |Microwave irradiation 3.1: 3,4,5-trimethoxyphenylboronic acid / toluene / 1 h / |Reflux; |Dean-Stark 3.2: 46 h / 100 °C / |Molecular sieve; |Sealed tube 3.3: 2 h / |Reflux 4.1: potassium carbonate / acetone / 4 h / |Reflux 5.1: ethanol / 14 h / |Reflux 6.1: pyridine / dichloromethane / 1.5 h / 0 - 20 °C 7.1: trichlorophosphate / acetonitrile / 1 h / |Reflux; |Inert atmosphere 8.1: [[(η6-p-cymene)((1S,2S)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine)]Ru]; formic acid; triethylamine / N,N-dimethyl-formamide / 20 °C 9.1: water; sodium hydroxide / ethanol / 3 h / 20 °C 10.1: thionyl chloride / dichloromethane / 1.5 h / 0 - 20 °C 11.1: sodium hydrogencarbonate / dichloromethane / 1.5 h / 20 °C 12.1: hydrogenchloride / water; ethanol / 2 h / |Reflux View Scheme
参考文献
Sun, Haifeng; Zhu, Liyuan; Yang, Huicui; Qian, Wangke; Guo, Lin; Zhou, Shengbin; Gao, Bo; Li, Zeng; Zhou, Yu; Jiang, Hualiang; Chen, Kaixian; Zhen, Xuechu; Liu, Hong
Bioorganic and Medicinal Chemistry, 2013 , vol. 21, # 4 p. 856 - 868
反应条件
1.1: potassium carbonate / N,N-dimethyl-formamide 2.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide 3.1: hydrogenchloride / methanol 4.1: potassium carbonate / N,N-dimethyl-formamide 5.1: piperidine; formic acid; palladium diacetate; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 3 h / 92 °C / Inert atmosphere 6.1: pyridine / 5 - 20 °C 7.1: methanol; water / 3 h / Reflux 8.1: water; sodium hydroxide / methanol / 2 h / Reflux 8.2: pH 2 View Scheme
参考文献
Nishimura, Koichiro; Kinugawa, Masahiko
Organic Process Research and Development, 2012 , vol. 16, # 2 p. 225 - 231
反应条件
1.1: potassium carbonate / acetone / |Reflux
2.1: potassium hydroxide; water; copper; copper(II) oxide / 1 h / 140 °C / |Inert atmosphere; |Microwave irradiation
3.1: 3,4,5-trimethoxyphenylboronic acid / toluene / 1 h / |Reflux; |Dean-Stark
3.2: 46 h / 100 °C / |Molecular sieve; |Sealed tube
3.3: 2 h / |Reflux
View Scheme
参考文献
SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES; LIU, Hong; XIE, Xin; ZHEN, Xuechu; SUN, Haifeng; LI, Jing; ZHU, Liyuan; LI, Zeng; CHEN, Ying; JIANG, Hualiang; CHEN, Kaixian
Patent: US2014/88130 A1, 2014 ;
反应条件
1.1: potassium carbonate / acetone / |Reflux
2.1: potassium hydroxide; water; copper; copper(II) oxide / 1 h / 140 °C / |Inert atmosphere; |Microwave irradiation
3.1: 3,4,5-trimethoxyphenylboronic acid / toluene / 1 h / |Reflux; |Dean-Stark
3.2: 46 h / 100 °C / |Molecular sieve; |Sealed tube
3.3: 2 h / |Reflux
4.1: potassium carbonate / acetone / 4 h / |Reflux
View Scheme
参考文献
Sun, Haifeng; Zhu, Liyuan; Yang, Huicui; Qian, Wangke; Guo, Lin; Zhou, Shengbin; Gao, Bo; Li, Zeng; Zhou, Yu; Jiang, Hualiang; Chen, Kaixian; Zhen, Xuechu; Liu, Hong
Bioorganic and Medicinal Chemistry, 2013 , vol. 21, # 4 p. 856 - 868
反应条件
1: NaOMe, MeOH
2: aq. NaOH
View Scheme
参考文献
Hellmann,H.; Elser,W.
Justus Liebigs Annalen der Chemie, 1961 , vol. 639, p. 77 - 88
