87546-18-7 (氟烯草酸,Flumiclorac-pentyl)

_93%

反应条件：

1.1 Catalysts: Acetic acid , Piperidine Solvents: Toluene ; 6 h, reflux

参考文献：

Synthesis of novel herbicide flumiclorac-pintyl

Lu, Yang; et al, Huagong Jishu Yu Kaifa, 2009, 38(6), 14-16

合成路线：1 步

123012-99-7

_93%

反应条件：

1.1 Catalysts: Acetic acid , Piperidine Solvents: Toluene ; 6 h, reflux

参考文献：

Synthesis of novel herbicide flumiclorac-pentyl

Lu, Yang; et al, Nongyao Kexue Yu Guanli, 2009, 30(6), 33-35

合成路线：1 步

123012-99-7

_92%

反应条件：

1.1 Catalysts: Acetic acid , Piperidine Solvents: Toluene ; rt → reflux; 6 h, reflux

参考文献：

Synthesis of 2-[2-chloro-4-fluoro-5-(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)phenoxy]acetic acid pentyl ester (flumiclorac-pentyl)

Zhang, Liyong; et al, Nongyao, 2007, 46(5), 307-309

合成路线：1 步

100004-30-6

反应条件：

1.1 Reagents: Sulfuryl chloride

参考文献：

3-Amino-4-fluorophenol

, Japan, , ,

合成路线：1 步

84478-41-1

52034-03-4

参考文献：

Tetrahydrophthalimide compounds and their use

, European Patent Organization, , ,

合成路线：2 步

123012-98-6

反应条件：

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ; rt → 0 °C; 5 - 6 h; 0.9 MPa; 1 MPa, 50 °C
2.1 Catalysts: Acetic acid , Piperidine Solvents: Toluene ; 6 h, reflux

参考文献：

Synthesis of novel herbicide flumiclorac-pintyl

Lu, Yang; et al, Huagong Jishu Yu Kaifa, 2009, 38(6), 14-16

合成路线：2 步

123012-98-6

反应条件：

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ; 0.9 MPa; 5 - 6 h, 1 MPa, 50 °C
2.1 Catalysts: Acetic acid , Piperidine Solvents: Toluene ; 6 h, reflux

参考文献：

Synthesis of novel herbicide flumiclorac-pentyl

Lu, Yang; et al, Nongyao Kexue Yu Guanli, 2009, 30(6), 33-35

合成路线：2 步

123012-98-6

反应条件：

1.1 Catalysts: Palladium , Carbon Solvents: Toluene ; 5 h, 1 MPa, rt
2.1 Reagents: Acetic acid Catalysts: Piperidine Solvents: Toluene ; 5 h, reflux

参考文献：

Study on new synthesis process of flumiclorac-pentyl

Tu, Mei-ling; et al, Zhejiang Gongye Daxue Xuebao, 2009, 37(2), 152-155

合成路线：2 步

84478-72-8

参考文献：

Tetrahydrophthalimide compounds and their use

, European Patent Organization, , ,

合成路线：3 步

1187183-55-6

反应条件：

1.1 Reagents: Sulfuric acid Solvents: Dichloromethane ; 50 °C
1.2 Reagents: Fuming nitric acid ; 1 h, 50 °C; 50 °C → 75 °C; 3 h, 75 °C
2.1 Catalysts: Palladium , Carbon Solvents: Toluene ; 5 h, 1 MPa, rt
3.1 Reagents: Acetic acid Catalysts: Piperidine Solvents: Toluene ; 5 h, reflux

参考文献：

Study on new synthesis process of flumiclorac-pentyl

Tu, Mei-ling; et al, Zhejiang Gongye Daxue Xuebao, 2009, 37(2), 152-155

合成路线：3 步

反应条件：

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ; 30 min, 45 °C
1.2 pH 9, 45 °C; 6 - 7 h, pH 9, 45 °C; 45 °C → 10 °C
2.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ; rt → 0 °C; 5 - 6 h; 0.9 MPa; 1 MPa, 50 °C
3.1 Catalysts: Acetic acid , Piperidine Solvents: Toluene ; 6 h, reflux

参考文献：

Synthesis of novel herbicide flumiclorac-pintyl

Lu, Yang; et al, Huagong Jishu Yu Kaifa, 2009, 38(6), 14-16

合成路线：3 步

反应条件：

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ; 30 min, 45 °C
1.2 pH 9, 45 °C; 6 - 7 h, pH 9, 45 °C; 45 °C → 10 °C
2.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ; 0.9 MPa; 5 - 6 h, 1 MPa, 50 °C
3.1 Catalysts: Acetic acid , Piperidine Solvents: Toluene ; 6 h, reflux

参考文献：

Synthesis of novel herbicide flumiclorac-pentyl

Lu, Yang; et al, Nongyao Kexue Yu Guanli, 2009, 30(6), 33-35

合成路线：3 步

反应条件：

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ; 20 min, 40 - 45 °C
1.2 1 h, 40 - 45 °C; 6 h, 40 - 45 °C; 45 °C → 20 °C
2.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ; 0.9 MPa; 5 h, 0.9 - 1.1 MPa, 50 - 55 °C
3.1 Catalysts: Acetic acid , Piperidine Solvents: Toluene ; rt → reflux; 6 h, reflux

参考文献：

Synthesis of 2-[2-chloro-4-fluoro-5-(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)phenoxy]acetic acid pentyl ester (flumiclorac-pentyl)

Zhang, Liyong; et al, Nongyao, 2007, 46(5), 307-309

合成路线：3 步

参考文献：

Tetrahydrophthalimide compounds and their use

, European Patent Organization, , ,

合成路线：4 步

153471-75-1

反应条件：

1.1 Reagents: Sodium hydroxide Solvents: Water
2.1 Reagents: Potassium carbonate Solvents: Dimethylformamide
3.1 Reagents: Acetic acid , Iron Solvents: Water
4.1 Reagents: Propionic acid , Piperidine Solvents: Toluene

参考文献：

Synthesis of herbicide flumiclorac-pentyl

Wu, Hao; et al, Nongyao, 2000, 39(11),

合成路线：4 步

1996-41-4

反应条件：

1.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ; 50 °C; 5 h, 80 °C
2.1 Reagents: Sulfuric acid Solvents: Dichloromethane ; 50 °C
2.2 Reagents: Fuming nitric acid ; 1 h, 50 °C; 50 °C → 75 °C; 3 h, 75 °C
3.1 Catalysts: Palladium , Carbon Solvents: Toluene ; 5 h, 1 MPa, rt
4.1 Reagents: Acetic acid Catalysts: Piperidine Solvents: Toluene ; 5 h, reflux

参考文献：

Study on new synthesis process of flumiclorac-pentyl

Tu, Mei-ling; et al, Zhejiang Gongye Daxue Xuebao, 2009, 37(2), 152-155

合成路线：4 步

1996-41-4

反应条件：

1.1 Reagents: Sodium hydroxide Catalysts: Tetrabutylammonium bromide Solvents: 1,2-Dichloroethane , Water ; 6 - 80 °C
1.2 Reagents: Triphosgene Solvents: 1,2-Dichloroethane ; 6 - 80 °C
1.3 Reagents: Sulfuric acid , Fuming nitric acid Solvents: Water ; 4 - 5 h, 80 °C
1.4 Reagents: Hydrochloric acid Solvents: Ethanol , Water ; 4 h, reflux; reflux → 10 °C
2.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ; 30 min, 45 °C
2.2 pH 9, 45 °C; 6 - 7 h, pH 9, 45 °C; 45 °C → 10 °C
3.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ; 0.9 MPa; 5 - 6 h, 1 MPa, 50 °C
4.1 Catalysts: Acetic acid , Piperidine Solvents: Toluene ; 6 h, reflux

参考文献：

Synthesis of novel herbicide flumiclorac-pentyl

Lu, Yang; et al, Nongyao Kexue Yu Guanli, 2009, 30(6), 33-35

合成路线：4 步

反应条件：

1.1 Reagents: Chlorine Solvents: 1,2-Dichloroethane ; 6 - 8 °C
1.2 Reagents: Sodium hydroxide , Triphosgene Catalysts: Tetrabutylammonium bromide Solvents: 1,2-Dichloroethane , Water ; 6 - 8 °C
1.3 Reagents: Sulfuric acid , Fuming nitric acid Solvents: Water ; rt; rt → 80 °C; 4 - 5 h, 80 °C
1.4 Reagents: Hydrochloric acid Solvents: Ethanol , Water ; 4 h, reflux; reflux → 10 °C
2.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ; 30 min, 45 °C
2.2 pH 9, 45 °C; 6 - 7 h, pH 9, 45 °C; 45 °C → 10 °C
3.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ; rt → 0 °C; 5 - 6 h; 0.9 MPa; 1 MPa, 50 °C
4.1 Catalysts: Acetic acid , Piperidine Solvents: Toluene ; 6 h, reflux

参考文献：

Synthesis of novel herbicide flumiclorac-pintyl

Lu, Yang; et al, Huagong Jishu Yu Kaifa, 2009, 38(6), 14-16

合成路线：4 步

反应条件：

1.1 Reagents: Chlorine Solvents: 1,2-Dichloroethane ; 3 - 4 h, 5 - 10 °C
1.2 Reagents: Sodium hydroxide Catalysts: Tetrabutylammonium bromide Solvents: Water ; 20 - 30 °C
1.3 Reagents: Phosgene Solvents: 1,2-Dichloroethane ; 3 h, 20 - 30 °C; 1 h, 20 - 30 °C
1.4 Reagents: Sulfuric acid , Fuming nitric acid Solvents: Water ; 1 h, 40 - 60 °C; 60 °C → 80 °C; 3 h, 75 - 80 °C
1.5 Reagents: Hydrochloric acid Solvents: Ethanol , Water ; 4 h, reflux; reflux → 10 °C
2.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ; 20 min, 40 - 45 °C
2.2 1 h, 40 - 45 °C; 6 h, 40 - 45 °C; 45 °C → 20 °C
3.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ; 0.9 MPa; 5 h, 0.9 - 1.1 MPa, 50 - 55 °C
4.1 Catalysts: Acetic acid , Piperidine Solvents: Toluene ; rt → reflux; 6 h, reflux

参考文献：

Synthesis of 2-[2-chloro-4-fluoro-5-(1,3,4,5,6,7-hexahydro-1,3-dioxo-2H-isoindol-2-yl)phenoxy]acetic acid pentyl ester (flumiclorac-pentyl)

Zhang, Liyong; et al, Nongyao, 2007, 46(5), 307-309

合成路线：5 步

反应条件：

1.1 Reagents: Chlorine Solvents: 1,2-Dichloroethane ; 6 - 8 °C
2.1 Reagents: Sodium hydroxide Catalysts: Tetrabutylammonium bromide Solvents: 1,2-Dichloroethane , Water ; 6 - 80 °C
2.2 Reagents: Triphosgene Solvents: 1,2-Dichloroethane ; 6 - 80 °C
2.3 Reagents: Sulfuric acid , Fuming nitric acid Solvents: Water ; 4 - 5 h, 80 °C
2.4 Reagents: Hydrochloric acid Solvents: Ethanol , Water ; 4 h, reflux; reflux → 10 °C
3.1 Reagents: Potassium carbonate Solvents: Dimethylformamide ; 30 min, 45 °C
3.2 pH 9, 45 °C; 6 - 7 h, pH 9, 45 °C; 45 °C → 10 °C
4.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ; 0.9 MPa; 5 - 6 h, 1 MPa, 50 °C
5.1 Catalysts: Acetic acid , Piperidine Solvents: Toluene ; 6 h, reflux

参考文献：

Synthesis of novel herbicide flumiclorac-pentyl

Lu, Yang; et al, Nongyao Kexue Yu Guanli, 2009, 30(6), 33-35

合成路线：4 步

84478-89-7

参考文献：

Tetrahydrophthalimide compounds and their use

, European Patent Organization, , ,

合成路线：5 步

541-41-3