131860-97-4

Basic information

• Product Name: Methyl (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylate
• Synonyms: METHYL (E)-2-[2-(6-CHLOROPYRIMIDIN-4-YLOXY)PHENYL]-3-METHOXYACRYLATE;2-[(6-Chloro-4-pyrimidinyl)oxy]-3-(methoxymethylene)benzeneacetic acid methyl ester;Benzeneacetic acid,2-[(6-chloro-4-pyriMidinyl)oxy]-a-(MethoxyMethylene)-, Methyl ester, (aE)-;(αE)-2-[(6-Chloro-4-pyriMidinyl)oxy]-α-(MethoxyMethylene)benzeneacetic Acid Methyl Ester;2-[2-[(6-chloro-4-pyrimidinyl)oxy]phenyl]-3-methoxy-2-propenoic acid methyl ester;methyl 2-[2-(6-chloropyrimidin-4-yl)oxyphenyl]-3-methoxyprop-2-enoate;(E)-Methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyacrylate;(2E)-2-(2-{[6-(2-Cyanophénoxy)-4-pyrimidinyl]oxy}phényl)-3-méthoxyacrylate de méthyle
• CAS NO: 131860-97-4
• Molecular Formula: C₁₅H₁₃ClN₂O₄
• Molecular Weight: 320.73
• Mol File: 131860-97-4.mol

Chemical Properties

• Boiling Point: 469.279 °C at 760 mmHg
• Flash Point: 237.612 °C
• Appearance: /
• Density: 1.305
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.574
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• PKA: -2.52±0.18(Predicted)
• CAS DataBase Reference: Methyl (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylate(131860-97-4)
• EPA Substance Registry System: Methyl (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylate(131860-97-4)

Safety Data

• Hazardous Substances Data: 131860-97-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methyl (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylate is used as an intermediate in the synthesis of Azoxystrobin (A965150), a strobilurin fungicide. This fungicide is effective in controlling various fungal diseases in crops, thereby improving agricultural productivity and crop quality.
Used in Chemical Synthesis:
Methyl (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylate can be used as a building block in the synthesis of other organic compounds, such as pharmaceuticals, agrochemicals, and specialty chemicals. Its unique structure allows for further functionalization and modification, making it a versatile component in organic synthesis.

InChI:InChI=1/C15H13ClN2O4/c1-20-8-11(15(19)21-2)10-5-3-4-6-12(10)22-14-7-13(16)17-9-18-14/h3-9H,1-2H3/b11-8+

Synthetic route

4,6-dichloropyrimidine (1193-21-1) + C12H15O5(1-)*Na(1+) → (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4)

Conditions	Yield
Stage #1: 4,6-dichloropyrimidine; C12H15O5(1-)*Na(1+) With sodium carbonate; methyl 1,4-diazabicyclo<2.2.2>octane-2-carboxylate In toluene at 20℃; for 2h; Stage #2: With zinc(II) chloride In toluene for 6h; Solvent; Reagent/catalyst; Reflux;	97.3%

methyl (Z)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylate → (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4)

Conditions	Yield
With methanesulfonic acid In acetonitrile at 70℃; for 8h;	96.9%

3-((α)‐2‐(2‐(6‐chloropyrimidin-4‐yl)oxy)phenyl)methyl-3-methoxyacrylate (383428-73-7) → (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4)

Conditions	Yield
With methanesulfonic acid for 1h; Heating; Large scale;	96%
With methanesulfonic acid In toluene at 85℃; for 1.5h; Large scale;

methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)acetate (484064-87-1) + dimethyl sulfate (77-78-1) + trimethyl orthoformate (149-73-5) → (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4)

Conditions	Yield
Stage #1: methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)acetate; trimethyl orthoformate With titanium tetrachloride; triethylamine In dichloromethane at -5 - 20℃; Inert atmosphere; Stage #2: dimethyl sulfate With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water; toluene at 20 - 50℃;	91%

4,6-dichloropyrimidine (1193-21-1) + (E)-3-methoxy-2-(2-hydroxyphenyl)-acrylic acid methyl ester (114077-42-8) → (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 0℃; Inert atmosphere;	84%
With caesium carbonate In N,N-dimethyl-formamide at 0℃; for 4h; Inert atmosphere;	84.6%
With potassium carbonate In N,N-dimethyl-formamide at 0℃; for 12h; Inert atmosphere;	83.1%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 15h;	67%

2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester (143230-42-6) → (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4)

Conditions	Yield
With toluene-4-sulfonic acid; sodium hydroxide In toluene at 80 - 90℃; for 3h;	82.3%
With methanesulfonic acid In acetic anhydride at 90℃; for 2h;	80%
With sodium hydrogencarbonate at 160℃; under 20 Torr; for 2h; Product distribution / selectivity;

4,6-dichloropyrimidine (1193-21-1) + (E)-Methyl 2-[2-hydroxyphenyl]-3-methoxypropenoate → (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	71%
With potassium carbonate In N,N-dimethyl-formamide
With potassium carbonate In N,N-dimethyl-formamide

2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester (143230-42-6) + methane sulfonic acid → (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4)

Conditions	Yield
With acetic anhydride In toluene

(E)-3-methoxy-2-(2-benzyloxyphenyl)acrylic acid methyl ester (103497-78-5) → (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 10% palladium on activated carbon; hydrogen / ethyl acetate / 6 h / 20 °C / 3040.2 Torr 2: caesium carbonate / N,N-dimethyl-formamide / 0 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 35 °C / 760.05 Torr 2: potassium carbonate / N,N-dimethyl-formamide / 12 h / 0 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: hydrogen; 5%-palladium/activated carbon / methanol / 18 h / 20 °C / 760.05 Torr 2: potassium carbonate / N,N-dimethyl-formamide / 15 h / 20 °C View Scheme

(Z)-3-methoxy-2-iodo-acrylic acid methyl ester (163041-47-2) → (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 10 h / 90 °C / Inert atmosphere 2: 10% palladium on activated carbon; hydrogen / ethyl acetate / 6 h / 20 °C / 3040.2 Torr 3: caesium carbonate / N,N-dimethyl-formamide / 0 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 10 h / 90 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 35 °C / 760.05 Torr 3: potassium carbonate / N,N-dimethyl-formamide / 12 h / 0 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 9.25 h / 20 - 90 °C / Sonication; Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 35 °C 3: caesium carbonate / N,N-dimethyl-formamide / 4 h / 0 °C / Inert atmosphere View Scheme

2-benzyloxyphenylboronic acid (190661-29-1) → (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 10 h / 90 °C / Inert atmosphere 2: 10% palladium on activated carbon; hydrogen / ethyl acetate / 6 h / 20 °C / 3040.2 Torr 3: caesium carbonate / N,N-dimethyl-formamide / 0 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 10 h / 90 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 35 °C / 760.05 Torr 3: potassium carbonate / N,N-dimethyl-formamide / 12 h / 0 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 9.25 h / 20 - 90 °C / Sonication; Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 35 °C 3: caesium carbonate / N,N-dimethyl-formamide / 4 h / 0 °C / Inert atmosphere View Scheme

2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylic acid (478413-47-7) + sodium methylate (124-41-4) → (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4)

Conditions	Yield
In methanol

3-(α-methoxy)methylene benzofuran-2-(3H)-ketone (40800-90-6) → (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium / 0.5 h / -10 °C 1.2: 1 h / Inert atmosphere 2.1: potassium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C 3.1: methanesulfonic acid / acetic anhydride / 2 h / 90 °C View Scheme
Multi-step reaction with 3 steps 1: 1 h / -5 - 0 °C 2: methyl 1,4-diazabicyclo<2.2.2>octane-2-carboxylate; sodium carbonate / toluene / 4 h / 20 °C 3: acetic anhydride; methanesulfonic acid / toluene / 8 h / 95 - 100 °C View Scheme
Multi-step reaction with 3 steps 1: polyethylene glycol 600 / tetrahydrofuran / 5 - 20 °C / Inert atmosphere; Large scale 2: sodium methylate / tetrahydrofuran / 75 h / 25 °C / Large scale 3: methanesulfonic acid / toluene / 1.5 h / 85 °C / Large scale View Scheme

2-(2-hydroxyphenyl)-3,3-dimethoxypropionic acid methyl ester (175971-61-6) → (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C 2: methanesulfonic acid / acetic anhydride / 2 h / 90 °C View Scheme
Multi-step reaction with 2 steps 1: sodium carbonate / toluene / 4 h / 20 °C 2: methanesulfonic acid; acetic anhydride / 6 h / 105 - 110 °C View Scheme
Multi-step reaction with 2 steps 1: methyl 1,4-diazabicyclo<2.2.2>octane-2-carboxylate; sodium carbonate / toluene / 4 h / 20 °C 2: acetic anhydride; methanesulfonic acid / toluene / 8 h / 95 - 100 °C View Scheme
Multi-step reaction with 2 steps 1: sodium carbonate / toluene / 4 h / 20 °C 2: acetic anhydride; methanesulfonic acid / toluene / 6 h / 105 - 110 °C View Scheme

2-Hydroxyphenylacetic acid (614-75-5) → (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 2-Methylpropionic anhydride / 10 h / 100 °C 2.1: sodium / 0.5 h / -10 °C 2.2: 1 h / Inert atmosphere 3.1: potassium carbonate / N,N-dimethyl-formamide / 8 h / 60 °C 4.1: methanesulfonic acid / acetic anhydride / 2 h / 90 °C View Scheme
Multi-step reaction with 5 steps 1.1: acetyl chloride; hydrogenchloride / 20 h / 20 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 10 h / 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide / 3 h 3.2: 2 h / 20 °C 4.1: hydrogen; 5%-palladium/activated carbon / methanol / 18 h / 20 °C / 760.05 Torr 5.1: potassium carbonate / N,N-dimethyl-formamide / 15 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1: acetic anhydride / 2.5 h / 110 °C / Inert atmosphere; Large scale 2: 21 h / 110 °C / Large scale 3: polyethylene glycol 600 / tetrahydrofuran / 5 - 20 °C / Inert atmosphere; Large scale 4: sodium methylate / tetrahydrofuran / 75 h / 25 °C / Large scale 5: methanesulfonic acid / toluene / 1.5 h / 85 °C / Large scale View Scheme
Multi-step reaction with 3 steps 1.1: acetic anhydride / 2 h / 100 °C / Inert atmosphere; Large scale 1.2: 19 h / 100 °C / Large scale 2.1: tetrahydrofuran; methanol / 72 h / 3 - 24 °C / Inert atmosphere; Large scale 3.1: methanesulfonic acid / 1 h / Heating; Large scale View Scheme

methyl (2E)-3-methoxy-2-propenoate (5788-17-0) → (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4)

Conditions

Yield

Multi-step reaction with 4 steps 1: iodine; pyridine / tetrachloromethane / 72 h / 0 - 20 °C / Inert atmosphere 2: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 10 h / 90 °C / Inert atmosphere 3: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 35 °C / 760.05 Torr 4: potassium carbonate / N,N-dimethyl-formamide / 12 h / 0 °C / Inert atmosphere View Scheme

2-bromophenyl benzyl ether (31575-75-4) → (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: magnesium; iodine / tetrahydrofuran / 2 h / 47 °C / Inert atmosphere 1.2: 4 h / -30 - 20 °C / Inert atmosphere 1.3: Grignard Reaction / 0.5 h / 20 °C 2.1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 10 h / 90 °C / Inert atmosphere 3.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 35 °C / 760.05 Torr 4.1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 0 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1.1: magnesium; iodine / tetrahydrofuran / 0.08 h / 35 - 47 °C / Inert atmosphere 1.2: 5 h / -30 °C / pH 2 2.1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 9.25 h / 20 - 90 °C / Sonication; Inert atmosphere 3.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 35 °C 4.1: caesium carbonate / N,N-dimethyl-formamide / 4 h / 0 °C / Inert atmosphere View Scheme

2-hydroxybromobenzene (95-56-7) → (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 3.5 h / 30 °C / Inert atmosphere 2.1: magnesium; iodine / tetrahydrofuran / 2 h / 47 °C / Inert atmosphere 2.2: 4 h / -30 - 20 °C / Inert atmosphere 2.3: Grignard Reaction / 0.5 h / 20 °C 3.1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 10 h / 90 °C / Inert atmosphere 4.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 35 °C / 760.05 Torr 5.1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 0 °C / Inert atmosphere View Scheme
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 3.5 h / 30 °C / Inert atmosphere 2.1: magnesium; iodine / tetrahydrofuran / 0.08 h / 35 - 47 °C / Inert atmosphere 2.2: 5 h / -30 °C / pH 2 3.1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 9.25 h / 20 - 90 °C / Sonication; Inert atmosphere 4.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 35 °C 5.1: caesium carbonate / N,N-dimethyl-formamide / 4 h / 0 °C / Inert atmosphere View Scheme

4,6-dichloropyrimidine (1193-21-1) + 3-(α-methoxy)methylene benzofuran-2-(3H)-ketone (40800-90-6) + sodium methylate (124-41-4) → 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester (143230-42-6) + (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4)

Conditions	Yield
With Methyl formate; potassium carbonate; 2-methyl-1,4-diazabicyclo [2,2,2]octane In methanol; toluene at 5 - 20℃; for 1.5h; Temperature; Reagent/catalyst; Time; Inert atmosphere; Overall yield = 92.7 %;
With trimethylamine In methanol; toluene at 5℃; for 6h; Catalytic behavior; Temperature; Reagent/catalyst;
With 3-dimethylamino-1-azabicyclo[2.2.2]octane In methanol; toluene at 5 - 15℃; for 2h;

benzofuran-2(3H)-one (553-86-6) → (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydride / N,N-dimethyl-formamide / 2 h / -10 - 0 °C 2: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C 3: sodium methylate / Methyl formate / 10 h / 20 - 25 °C View Scheme
Multi-step reaction with 4 steps 1: 21 h / 110 °C / Large scale 2: polyethylene glycol 600 / tetrahydrofuran / 5 - 20 °C / Inert atmosphere; Large scale 3: sodium methylate / tetrahydrofuran / 75 h / 25 °C / Large scale 4: methanesulfonic acid / toluene / 1.5 h / 85 °C / Large scale View Scheme
Multi-step reaction with 3 steps 1: acetic anhydride / 95 - 100 °C 2: sodium methylate / toluene / 20 - 25 °C 3: toluene-4-sulfonic acid; sodium hydroxide / toluene / 3 h / 80 - 90 °C View Scheme
Multi-step reaction with 3 steps 1: water / 12 h / 100 °C / Autoclave 2: sodium / 1 h / 0 °C 3: sodium / 1 h / 0 °C View Scheme

3-formylbenzofuran-2(3H)-one (40800-88-2) → (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C 2: sodium methylate / Methyl formate / 10 h / 20 - 25 °C View Scheme

4,6-dichloropyrimidine (1193-21-1) + 3-(α-methoxy)methylene benzofuran-2-(3H)-ketone (40800-90-6) → (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4)

Conditions	Yield
With sodium methylate In Methyl formate at 20 - 25℃; for 10h;

methyl 3-methoxyprop-2-enoate (34846-90-7) → (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4)

Conditions

Yield

Multi-step reaction with 4 steps 1: pyridine; iodine / tetrachloromethane / 72 h / 0 - 20 °C / Inert atmosphere 2: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 9.25 h / 20 - 90 °C / Sonication; Inert atmosphere 3: palladium 10% on activated carbon; hydrogen / ethyl acetate / 12 h / 35 °C 4: caesium carbonate / N,N-dimethyl-formamide / 4 h / 0 °C / Inert atmosphere View Scheme

methyl (2-hydroxyphenyl)acetate (22446-37-3) → (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 10 h / 20 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 3 h 2.2: 2 h / 20 °C 3.1: hydrogen; 5%-palladium/activated carbon / methanol / 18 h / 20 °C / 760.05 Torr 4.1: potassium carbonate / N,N-dimethyl-formamide / 15 h / 20 °C View Scheme

2-benzyloxyphenylacetic acid methyl ester (40525-65-3) → (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 3 h 1.2: 2 h / 20 °C 2.1: hydrogen; 5%-palladium/activated carbon / methanol / 18 h / 20 °C / 760.05 Torr 3.1: potassium carbonate / N,N-dimethyl-formamide / 15 h / 20 °C View Scheme

4,6-dichloropyrimidine (1193-21-1) + 3-(α-methoxy)methylene benzofuran-2-(3H)-ketone (40800-90-6) → 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester (143230-42-6) + (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4)

Conditions	Yield
With sodium methylate; potassium carbonate; 2-methyl-1,4-diazabicyclo [2,2,2]octane In methanol; Methyl formate; toluene at 5 - 20℃; for 1.5h; Reagent/catalyst; Temperature; Inert atmosphere; Overall yield = 92.3 %Chromat.;

(E)-3-(α-methoxy)methylenebenzofuran-2(3H)-one (40800-90-6) → (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: methanol / 1 h / -5 - 0 °C 2: sodium carbonate / toluene / 4 h / 20 °C 3: methanesulfonic acid; acetic anhydride / 6 h / 105 - 110 °C View Scheme

methyl 2-(2-hydroxyphenyl)-3-methoxyacrylate (125808-20-0) → (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium methylate / tetrahydrofuran / 75 h / 25 °C / Large scale 2: methanesulfonic acid / toluene / 1.5 h / 85 °C / Large scale View Scheme

3-(α-methoxy)methylene benzofuran-2-(3H)-ketone (40800-90-6) → 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester (143230-42-6) + (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1 h / -5 - 0 °C 2: sodium carbonate; methyl 1,4-diazabicyclo<2.2.2>octane-2-carboxylate / toluene / 2 h / 20 °C View Scheme

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4) → azoxystrobin (215934-32-0, 131860-33-8)

Conditions	Yield
Stage #1: salicylonitrile With potassium carbonate; 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 60℃; for 0.166667h; Stage #2: (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate In N,N-dimethyl-formamide at 60 - 84℃; for 0.333333h; Product distribution / selectivity;	100%
Stage #1: salicylonitrile With potassium carbonate In cyclohexanone at 100℃; for 0.166667h; Stage #2: (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate; 1,4-diaza-bicyclo[2.2.2]octane In cyclohexanone at 100℃; for 1.66667h; Product distribution / selectivity;	96.3%
Stage #1: salicylonitrile; 1,4-diaza-bicyclo[2.2.2]octane In toluene at 70℃; for 0.5h; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 70 - 74℃; for 0.25h; Stage #3: (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate In toluene at 70℃; for 0.5h; Product distribution / selectivity;	94.7%

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4) + salicylonitrile (611-20-1) → azoxystrobin (215934-32-0, 131860-33-8)

Conditions	Yield
With potassium carbonate; quinuclidine hydrochloride In 4-methyl-2-pentanone at 60 - 80℃; for 0.5h; Product distribution / selectivity;	100%
With potassium carbonate; 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 48 - 65℃; for 1h; Product distribution / selectivity;	98.3%
Stage #1: (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate; salicylonitrile In N,N-dimethyl-formamide at 60℃; for 0.0833333h; Stage #2: 1,4-diaza-bicyclo[2.2.2]octane In N,N-dimethyl-formamide at 60℃; for 0.0833333h; Stage #3: With potassium carbonate In N,N-dimethyl-formamide at 60 - 89℃; for 0.166667h; Product distribution / selectivity;	97.1%

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4) + 2-hydroxybenzonitrile potassium salt → azoxystrobin (215934-32-0, 131860-33-8)

Conditions	Yield
With potassium carbonate; triethylamine In water; toluene at 80℃; for 10h;	96.12%

2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester (143230-42-6) + (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4) + salicylonitrile (611-20-1) → 2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]-3,3-dimethoxypropionic acid methyl ester + azoxystrobin (215934-32-0, 131860-33-8)

Conditions	Yield
Stage #1: 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester; (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate; salicylonitrile With potassium carbonate In Isopropyl acetate at 60℃; for 0.166667h; Stage #2: With 1,4-diaza-bicyclo[2.2.2]octane In Isopropyl acetate at 90℃; for 6h; Product distribution / selectivity;	A 91.45% B 4.4%
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate In Isopropyl acetate for 6.5h; Product distribution / selectivity; Heating / reflux;	A 82.85% B 7.05%
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate In cyclohexanone at 90℃; for 2.33333 - 4h; Product distribution / selectivity;	A 73% B 18.3%

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4) + tert-butyl 6-(3-cyano-4-hydroxyphenyl)hexanoate (1266105-23-0) → tert-butyl 6-(3-cyano-4-(6-(2-((E)-1-(methoxycarbonyl)-2-methoxyvinyl)phenoxy) pyrimidin-4-yloxy)phenyl)hexanoate (1266105-24-1)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 85℃; for 3h; Inert atmosphere;	91%

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4) + sodium thiomethoxide (5188-07-8) → (E)-methyl 2-[2-(6-(2-cyanoanilino)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (141190-17-2) + (E)-methyl 2-[2-(6-methylthiopyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (131860-99-6)

Conditions	Yield
tetrabutylammomium bromide In chloroform; water	A 89% B n/a

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4) + ethyl 2-(2-hydroxyphenyl)acetate (41873-65-8) → C25H24N2O7

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;	89%

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4) + toluene-3-thiol (108-40-7) → C22H20N2O4S

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;	88%

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4) + 2-thiocresol (137-06-4) → C22H20N2O4S

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;	85%

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4) + ortho-cresol (95-48-7) → C22H20N2O5

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;	85%

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4) + para-thiocresol (106-45-6) → C22H20N2O4S

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;	82%

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4) + methyl salicylate (119-36-8) → C23H20N2O7

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;	82%

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4) + 2-hydroxybenzonitrile sodium salt (74255-21-3) → azoxystrobin (215934-32-0, 131860-33-8)

Conditions	Yield
With silica gel immobilized triethylene diamine catalyst 2 In toluene at 80 - 85℃; for 5h;	82%

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4) + 4-hydroxybenzotrifluoride (402-45-9) → C22H17F3N2O5

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;	81%

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4) + phenol (108-95-2) → (E)-methyl 3-methoxy-2-(2-(6-phenoxypyrimidin-4-yloxy)phenyl)acrylate (131860-27-0)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 85℃; for 3h;	80%

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4) + 1-(4-chlorophenyl)-1H-pyrazol-4-ol (77458-30-1) → C24H19ClN4O5

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;	79%

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4) + 3-Trifluoromethylphenol (98-17-9) → C22H17F3N2O5

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;	76%

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4) + salicylonitrile (611-20-1) + azoxystrobin (215934-32-0, 131860-33-8) → 2-hydroxybenzonitrile potassium salt

Conditions	Yield
With potassium carbonate In water	75.6%
With potassium carbonate In water	70.8%
With potassium hydroxide In water	61.5%

2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester (143230-42-6) + (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4) + 2-hydroxybenzonitrile potassium salt → 2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]-3,3-dimethoxypropionic acid methyl ester + azoxystrobin (215934-32-0, 131860-33-8)

Conditions	Yield
Stage #1: 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester; (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate; 2-hydroxybenzonitrile potassium salt With potassium carbonate In Isopropyl acetate; water at 50℃; Stage #2: With 1,4-diaza-bicyclo[2.2.2]octane In Isopropyl acetate; water for 3.75 - 5h; Product distribution / selectivity; Heating / reflux;	A 72.6% B 15.4%
Stage #1: 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester; (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate In Isopropyl acetate; water at 50℃; Stage #2: 2-hydroxybenzonitrile potassium salt In Isopropyl acetate; water for 4.33333h; Product distribution / selectivity; Heating / reflux;	A 68% B 12.4%

4,5-dichloropyrimidine (6554-61-6) + (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4) + (E)-Methyl 2-[2-hydroxyphenyl]-3-methoxypropenoate + 2-chloro-3-hydroxypyridine (6636-78-8) → (E)-methyl 2-[2-(6-(2-chloropyrid-3-yloxy)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (133001-57-7)

Conditions	Yield
With potassium carbonate; copper(I) chloride In N,N-dimethyl-formamide	70%

methanol (67-56-1) + (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4) → C16H16N2O5

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;	69%

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate (131860-97-4) + 3-[(4-hydroxyphenyl)imino]-5-methyl-1-propylindolin-2-one → (E)-methyl 3-methoxy-2-(2-((6-(4-((5-methyl-2-oxo-1-propylindolin-3-ylidene)amino)phenoxy)pyrimidin-4-yl)oxy)phenyl)acrylate

Conditions	Yield
Stage #1: 3-[(4-hydroxyphenyl)imino]-5-methyl-1-propylindolin-2-one With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 0.5h; Stage #2: (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate In N,N-dimethyl-formamide at 90℃;	69%

Upstream product

• 1193-21-1 4,6-dichloropyrimidine 
• 40800-90-6 3-(α-methoxy)methylene benzofuran-2-(3H)-ketone 
• 175971-61-6 2-(2-hydroxyphenyl)-3,3-dimethoxypropionic acid methyl ester 
• 614-75-5 2-Hydroxyphenylacetic acid 
• 553-86-6 benzofuran-2(3H)-one 
• 40800-88-2 3-formylbenzofuran-2(3H)-one 
• 34846-90-7 methyl 3-methoxyprop-2-enoate 
• 22446-37-3 methyl (2-hydroxyphenyl)acetate 
• 40525-65-3 2-benzyloxyphenylacetic acid methyl ester 
• 40800-90-6 (E)-3-(α-methoxy)methylenebenzofuran-2(3H)-one 
• 2444-36-2 2'-chloro-benzeneacetic acid 
• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 107-31-3 Methyl formate 

Downstream Products

• 215934-32-0 azoxystrobin 
• 141190-17-2 (E)-methyl 2-[2-(6-(2-cyanoanilino)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate 
• 131860-99-6 (E)-methyl 2-[2-(6-methylthiopyrimidin-4-yloxy)phenyl]-3-methoxypropenoate 
• 133001-57-7 (E)-methyl 2-[2-(6-(2-chloropyrid-3-yloxy)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate 
• 133001-62-4 (E)-methyl 2-[2-(6-(6-chloropyrid-2-yloxy)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate 
• 1266105-24-1 tert-butyl 6-(3-cyano-4-(6-(2-((E)-1-(methoxycarbonyl)-2-methoxyvinyl)phenoxy) pyrimidin-4-yloxy)phenyl)hexanoate 
• 1266105-09-2 6-(3-cyano-4-(6-(2-((E)-1-(methoxycarbonyl)-2-methoxyvinyl)phenoxy)pyrimidin-4-yloxy) phenyl)hexanoic acid 
• 131860-27-0 (E)-methyl 3-methoxy-2-(2-(6-phenoxypyrimidin-4-yloxy)phenyl)acrylate 
• 1547325-32-5 4-{6-[2-(2-methoxy-1-methoxycarbonylvinyl)phenoxy]pyrimidin-4-yloxy}-7-methyl-6-tetradecyloxyquinoline-3-carboxylic acid ethyl ester 
• 1547325-35-8 6-hexadecyloxy-4-{6-[2-(2-methoxy-1-methoxycarbonylvinyl)phenoxy]pyrimidin-4-yloxy}-7-methylquinoline-3-carboxylic acid ethyl ester 
• 1547325-36-9 6-decyloxy-4-{6-[2-(2-methoxy-1-methoxycarbonylvinyl)phenoxy]pyrimidin-4-yloxy}-7-methylquinoline-3-carboxylic acid ethyl ester 
• 1547325-39-2 4-{6-[2-(2-methoxy-1-methoxycarbonylvinyl)phenoxy]pyrimidin-4-yloxy}-7-methyl-6-octyloxyquinoline-3-carboxylic acid ethyl ester 
• 1547325-41-6 6-decyloxy-7-ethoxy-4-{6-[2-(2-methoxy-1-methoxycarbonylvinyl)phenoxy]pyrimidin-4-yloxy}quinoline-3-carboxylic acid ethyl ester 
• 1547325-43-8 6-dodecyloxy-4-{6-[2-(2-methoxy-1-methoxycarbonylvinyl)phenoxy]pyrimidin-4-yloxy}-7-methylquinoline-3-carboxylic acid ethyl ester 

Relevant articles and documents

Preparation method of azoxystrobin intermediate

The invention relates to the technical field of preparation of pesticide intermediates, in particular to a preparation method of an azoxystrobin intermediate. The invention relates to a preparation method of an azoxystrobin intermediate, which comprises the following steps: putting methoxymethylene benzofuranone and dichloropyrimidine into a solvent, adding alkali and a catalyst to carry out ring-opening reaction, adding alkali again, and carrying out etherification reaction to synthesize an azoxystrobin intermediate compound (E)-2-[2-(6-chloropyrimidine-4-methoxy) phenyl]-3methoxy methyl acrylate C; the reaction formula is disclosed in the invention; the structural formula of the catalyst is selected from any one disclosed in the invention; according to the invention, reaction is selectively carried out on the ring opening of methoxymethylene benzofuranone, Michael addition is inhibited, the generation of by-products B is reduced, and the problem of low efficiency of catalysts such asDABCO, trimethylamine and the like is solved at the same time.

Method for improving conversion rate of azoxystrobin

The invention discloses a method for improving the conversion rate of azoxystrobin. The method comprises the following steps: preparing methyl (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy acrylate; preparing o-hydroxybenzonitrile; mixing methyl (E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy acrylate, o-hydroxybenzonitrile, potassium carbonate and ketene chloride according to a molar ratio of 30: 35: 50: 1.1, and dissolving the obtained mixture in dimethylformamide to obtain a mixed product; and heating the prepared mixed product, keeping the mixed product at a certain temperature, conducting filtering, carrying out reduced-pressure distillation, performing cooling, separating out crystals, carrying out filtering and washing and performing drying to obtain azoxystrobin. On the basis of the prior art, the synthesis of azoxystrobin is improved in the invention, so the yield of azoxystrobin is effectively increased, the conversion rate of the raw materials including methyl(E)-2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy acrylate and o-hydroxybenzonitrile for azoxystrobin in the process of preparing azoxystrobin is effectively improved, and the production benefit of azoxystrobin is improved.

PROCESS FOR THE PREPARATION OF FUNGICIDALLY ACTIVE STROBILURIN COMPOUNDS AND INTERMEDIATES THEREOF

The present invention relates to a process for the preparation of strobilurin of compounds of Formula (I) of and its intermediates using 1,5,7-triazabicyclo[4.4.0]dec-5-ene or salts thereof, or derivatives thereof as a catalyst. The present invention provides the compounds of formula (I) in high yield and high purity.

PROCESS FOR PREPARATION OF AZOXYSTROBIN AND INTERMEDIATES THEREOF

The present invention relates to a process for preparation of strobilurin compound, azoxystrobin and its intermediates using a catalyst selected from 1,8-Diazabicyclo[5.4.0]undec-7-ene or 1,5-Diazabicyclo[4.3.0]non-5-ene, salts thereof, or derivatives thereof.

Preparation method of azoxystrobin compound

The present invention relates to the field of chemical synthesis, and discloses a preparation method of azoxystrobin compounds, which comprises steps that a compound represented by a formula (II) is adopted as a raw material to carry out a reaction, wherein R is halogen, a hydroxyl group or a 2-cyanophenoxy group. According to the method disclosed by the invention, the pure azoxystrobin compound can be simply and conveniently obtained, a complex separation and purification process is avoided, the waste of raw materials is reduced, and the atom utilization rate is improved.

An azoxystrobin and its intermediate synthesis method

The invention discloses a synthesis method for azoxystrobin. The synthesis method comprises the following steps of reacting a mixed system containing (E)-methyl-2-[2-(6-chloropyrimidine-4-methoxy) phenyl]-3-methoxyacrylate and methyl 2-[2-(6-chloropyrimidine-4-methoxy) phenyl]-3,3-dimethoxypropanoate with 2-hydroxy-benzonitril in the presence of a catalyst, adding metal chloride, and performing heating reaction and post-treatment to obtain azoxystrobin. The synthesis method is mild in reaction condition, and reaction can be realized under the conditions of normal pressure and negative pressure; moreover, the use of a hypertoxic catalyst such as dimethyl sulfate is avoided in a reaction process, so that safety is greatly improved, and environmental pollution is greatly reduced; the synthesis method is pure in reaction, and fewer byproducts are produced.

A process for preparing a azoxystrobin or intermediate catalyst and preparation method (by machine translation)

The invention relates to a process for the preparation of azoxystrobin or intermediate catalyst, containing 1 - azabicyclo [2, 2, 2] octane structure on a series of compounds introduced into the amino or substituted amino, form the formula 10 structure shown or a salt thereof; the invention also relates to processes for preparing azoxystrobin or intermediates thereof, the present invention provides catalyst and preparation method, with process is easy to control, short reaction time, the conversion is high, and low energy consumption, and is suitable for large-scale industrial production. (by machine translation)

Preparation method of azoxystrobin

The invention discloses a preparation method of azoxystrobin. The preparation method of the azoxystrobin particularly comprises the following steps: performing reaction on hydroxyphenylacetic acid serving as a starting material and trimethyl orthoformate to generate 3-(alpha-methoxy)-methylene benzofuran-2-(3 hydrogen)-ketone, performing reaction on 3-(alpha-methoxy)-methylene benzofuran-2-(3 hydrogen)-ketone, sodium methylate and 4,6-dichloropyrimidine to obtain 3-((alpha)-2-(2-(6-chloropyrimidine-4-yl oxy)phenyl)-methyl 3-methoxyacrylate, performing reaction on 3-((alpha)-2-(2-(6-chloropyrimidine-4-oxy)phenyl)-methyl 3-methoxyacrylate, methanesulfonic acid and methylbenzene to obtain (E)-2-(2-(6-chloropyrimidine-4-yl oxy)phenyl)-methyl 3-methoxyacrylate, and finally performing reaction on (E)-2-(2-(6-chloropyrimidine-4-yl oxy)phenyl)-methyl 3-methoxyacrylate, hydroxybenzonitrile, potassium carbonate, ferric oxide and the like to obtain the azoxystrobin. According to the preparation method provided by the invention, the reaction process is easy to control and the yield of the prepared product is high.

Method for preparing azoxystrobin intermediates

The present invention provides a method for preparing azoxystrobin intermediates, comprising reacting compound A and dichloropyrimidine in the presence of a trimethylamine catalyst with the addition of a sodium methoxide solution in methanol or the addition of sodium methoxide and methanol separately to produce a mixture of compound B and compound C. Azoxystrobin intermediate compound B and compound C are synthesized from compound A in the present invention, which is catalyzed by using a trimethylamine catalyst, allowing the reaction to have high efficiency and high yield. In addition, the trimethylamine catalyst has a low boiling point and thus can be easily recycled so that the ammoniacal nitrogen content in wastewater can be reduced, and the difficulties and high costs for wastewater processing can be also reduced. The recycled trimethylamine catalyst can be reused in preparing intermediate compound B, which also has a high catalytic effect and can also achieve a high product yield. The method of the present invention has significant synthetical cost advantages and is suitable for industrial production.

Compounding method for azoxystrobin

The invention discloses a compounding method for azoxystrobin. The method comprises the following steps: compounding 3-(-methoxy)-methanoisobenzofuran-2(3-hydrogen-)-hydrogen; compounding 3-((alpha)-2-(2-(6-chloropyrimidine-4-oxygen) phenyl)-3-methyl methoxyacrylate; compounding (E)-2-(2-(6-chloropyrimidine-4-oxygen) phenyl)-3-methyl methoxyacrylate; and compounding azoxystrobin. The compounding method for azoxystrobin, provided by the invention, is characterized by simple operation steps, mild reaction conditions, low operation difficulty, low energy consumption, environment-friendly compounding process, less wastewater and waste emission, easiness in treatment, high yield of obtained azoxystrobin, reusable reagent, reduction of reagent consumption, low compounding cost, capability of realizing clean production and being worthy of popularization.