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131860-97-4

131860-97-4

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131860-97-4 Usage

Uses

(αE)-2-[(6-chloro-4-pyrimidinyl)oxy]-α-(methoxymethylene)benzeneacetic Acid Methyl Ester is an intermediate in the synthesis of Azoxystrobin (A965150), an strobilurin fungicide.

Check Digit Verification of cas no

The CAS Registry Mumber 131860-97-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,1,8,6 and 0 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 131860-97:
(8*1)+(7*3)+(6*1)+(5*8)+(4*6)+(3*0)+(2*9)+(1*7)=124
124 % 10 = 4
So 131860-97-4 is a valid CAS Registry Number.
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+

131860-97-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name methyl 2-[2-(6-chloropyrimidin-4-yl)oxyphenyl]-3-methoxyprop-2-enoate

1.2 Other means of identification

Product number -
Other names (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxypropenoate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:131860-97-4 SDS

131860-97-4Synthetic route

4,6-dichloropyrimidine
1193-21-1

4,6-dichloropyrimidine

C12H15O5(1-)*Na(1+)

C12H15O5(1-)*Na(1+)

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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
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

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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
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

3-((α)‐2‐(2‐(6‐chloropyrimidin-4‐yl)oxy)phenyl)methyl-3-methoxyacrylate

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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
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

methyl 2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)acetate

dimethyl sulfate
77-78-1

dimethyl sulfate

trimethyl orthoformate
149-73-5

trimethyl orthoformate

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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
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

4,6-dichloropyrimidine

(E)-3-methoxy-2-(2-hydroxyphenyl)-acrylic acid methyl ester
114077-42-8

(E)-3-methoxy-2-(2-hydroxyphenyl)-acrylic acid methyl ester

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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
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

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
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
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

4,6-dichloropyrimidine

(E)-Methyl 2-[2-hydroxyphenyl]-3-methoxypropenoate

(E)-Methyl 2-[2-hydroxyphenyl]-3-methoxypropenoate

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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide71%
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

2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester

methane sulfonic acid

methane sulfonic acid

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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
With acetic anhydride In toluene
(E)-3-methoxy-2-(2-benzyloxyphenyl)acrylic acid methyl ester
103497-78-5

(E)-3-methoxy-2-(2-benzyloxyphenyl)acrylic acid methyl ester

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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
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

(Z)-3-methoxy-2-iodo-acrylic acid methyl ester

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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
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

2-benzyloxyphenylboronic acid

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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
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

2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxyacrylic acid

sodium methylate
124-41-4

sodium methylate

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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
In methanol
3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
40800-90-6

3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
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

2-(2-hydroxyphenyl)-3,3-dimethoxypropionic acid methyl ester

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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
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

2-Hydroxyphenylacetic acid

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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
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

methyl (2E)-3-methoxy-2-propenoate

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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
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

2-bromophenyl benzyl ether

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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
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

2-hydroxybromobenzene

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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
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

4,6-dichloropyrimidine

3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
40800-90-6

3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

sodium methylate
124-41-4

sodium methylate

A

2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester
143230-42-6

2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester

B

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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
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

benzofuran-2(3H)-one

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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
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

3-formylbenzofuran-2(3H)-one

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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
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

4,6-dichloropyrimidine

3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
40800-90-6

3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
With sodium methylate In Methyl formate at 20 - 25℃; for 10h;
methyl 3-methoxyprop-2-enoate
34846-90-7

methyl 3-methoxyprop-2-enoate

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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
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

methyl (2-hydroxyphenyl)acetate

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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
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

2-benzyloxyphenylacetic acid methyl ester

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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
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

4,6-dichloropyrimidine

3-(α-methoxy)methylene benzofuran-2-(3H)-ketone
40800-90-6

3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

A

2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester
143230-42-6

2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester

B

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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
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)-3-(α-methoxy)methylenebenzofuran-2(3H)-one

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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
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

methyl 2-(2-hydroxyphenyl)-3-methoxyacrylate

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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
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

3-(α-methoxy)methylene benzofuran-2-(3H)-ketone

A

2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester
143230-42-6

2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester

B

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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

Conditions
ConditionsYield
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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

azoxystrobin
215934-32-0, 131860-33-8

azoxystrobin

Conditions
ConditionsYield
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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

salicylonitrile
611-20-1

salicylonitrile

azoxystrobin
215934-32-0, 131860-33-8

azoxystrobin

Conditions
ConditionsYield
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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

2-hydroxybenzonitrile potassium salt

2-hydroxybenzonitrile potassium salt

azoxystrobin
215934-32-0, 131860-33-8

azoxystrobin

Conditions
ConditionsYield
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

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
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

salicylonitrile
611-20-1

salicylonitrile

A

2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]-3,3-dimethoxypropionic acid methyl ester

2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]-3,3-dimethoxypropionic acid methyl ester

B

azoxystrobin
215934-32-0, 131860-33-8

azoxystrobin

Conditions
ConditionsYield
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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

tert-butyl 6-(3-cyano-4-hydroxyphenyl)hexanoate
1266105-23-0

tert-butyl 6-(3-cyano-4-hydroxyphenyl)hexanoate

tert-butyl 6-(3-cyano-4-(6-(2-((E)-1-(methoxycarbonyl)-2-methoxyvinyl)phenoxy) pyrimidin-4-yloxy)phenyl)hexanoate
1266105-24-1

tert-butyl 6-(3-cyano-4-(6-(2-((E)-1-(methoxycarbonyl)-2-methoxyvinyl)phenoxy) pyrimidin-4-yloxy)phenyl)hexanoate

Conditions
ConditionsYield
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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

sodium thiomethoxide
5188-07-8

sodium thiomethoxide

A

(E)-methyl 2-[2-(6-(2-cyanoanilino)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate
141190-17-2

(E)-methyl 2-[2-(6-(2-cyanoanilino)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate

B

(E)-methyl 2-[2-(6-methylthiopyrimidin-4-yloxy)phenyl]-3-methoxypropenoate
131860-99-6

(E)-methyl 2-[2-(6-methylthiopyrimidin-4-yloxy)phenyl]-3-methoxypropenoate

Conditions
ConditionsYield
tetrabutylammomium bromide In chloroform; waterA 89%
B n/a
(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

ethyl 2-(2-hydroxyphenyl)acetate
41873-65-8

ethyl 2-(2-hydroxyphenyl)acetate

C25H24N2O7

C25H24N2O7

Conditions
ConditionsYield
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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

toluene-3-thiol
108-40-7

toluene-3-thiol

C22H20N2O4S

C22H20N2O4S

Conditions
ConditionsYield
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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

2-thiocresol
137-06-4

2-thiocresol

C22H20N2O4S

C22H20N2O4S

Conditions
ConditionsYield
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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

ortho-cresol
95-48-7

ortho-cresol

C22H20N2O5

C22H20N2O5

Conditions
ConditionsYield
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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

para-thiocresol
106-45-6

para-thiocresol

C22H20N2O4S

C22H20N2O4S

Conditions
ConditionsYield
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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

methyl salicylate
119-36-8

methyl salicylate

C23H20N2O7

C23H20N2O7

Conditions
ConditionsYield
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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

2-hydroxybenzonitrile sodium salt
74255-21-3

2-hydroxybenzonitrile sodium salt

azoxystrobin
215934-32-0, 131860-33-8

azoxystrobin

Conditions
ConditionsYield
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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

4-hydroxybenzotrifluoride
402-45-9

4-hydroxybenzotrifluoride

C22H17F3N2O5

C22H17F3N2O5

Conditions
ConditionsYield
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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

phenol
108-95-2

phenol

(E)-methyl 3-methoxy-2-(2-(6-phenoxypyrimidin-4-yloxy)phenyl)acrylate
131860-27-0

(E)-methyl 3-methoxy-2-(2-(6-phenoxypyrimidin-4-yloxy)phenyl)acrylate

Conditions
ConditionsYield
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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

1-(4-chlorophenyl)-1H-pyrazol-4-ol
77458-30-1

1-(4-chlorophenyl)-1H-pyrazol-4-ol

C24H19ClN4O5

C24H19ClN4O5

Conditions
ConditionsYield
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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

3-Trifluoromethylphenol
98-17-9

3-Trifluoromethylphenol

C22H17F3N2O5

C22H17F3N2O5

Conditions
ConditionsYield
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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

salicylonitrile
611-20-1

salicylonitrile

azoxystrobin
215934-32-0, 131860-33-8

azoxystrobin

2-hydroxybenzonitrile potassium salt

2-hydroxybenzonitrile potassium salt

Conditions
ConditionsYield
With potassium carbonate In water75.6%
With potassium carbonate In water70.8%
With potassium hydroxide In water61.5%
2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropionic acid methyl ester
143230-42-6

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
131860-97-4

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

2-hydroxybenzonitrile potassium salt

2-hydroxybenzonitrile potassium salt

A

2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]-3,3-dimethoxypropionic acid methyl ester

2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]-3,3-dimethoxypropionic acid methyl ester

B

azoxystrobin
215934-32-0, 131860-33-8

azoxystrobin

Conditions
ConditionsYield
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

4,5-dichloropyrimidine

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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

(E)-Methyl 2-[2-hydroxyphenyl]-3-methoxypropenoate

(E)-Methyl 2-[2-hydroxyphenyl]-3-methoxypropenoate

2-chloro-3-hydroxypyridine
6636-78-8

2-chloro-3-hydroxypyridine

(E)-methyl 2-[2-(6-(2-chloropyrid-3-yloxy)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate
133001-57-7

(E)-methyl 2-[2-(6-(2-chloropyrid-3-yloxy)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate

Conditions
ConditionsYield
With potassium carbonate; copper(I) chloride In N,N-dimethyl-formamide70%
methanol
67-56-1

methanol

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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

C16H16N2O5

C16H16N2O5

Conditions
ConditionsYield
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

(E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxy-propenoate

3-[(4-hydroxyphenyl)imino]-5-methyl-1-propylindolin-2-one

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

(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
ConditionsYield
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%

131860-97-4Downstream Products

131860-97-4Relevant articles and documents

Preparation method of azoxystrobin intermediate

-

Paragraph 0041-0058, (2021/08/06)

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.

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

-

Page/Page column 48; 49, (2020/10/28)

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.

Preparation method of azoxystrobin compound

-

Paragraph 0061-0066, (2019/12/02)

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.

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