Potassium Carbonate → Azoxystrobin

HRID 1859234Notes

Reaction equation

HRID 1859234 reaction equation
[K].[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])#[N:3].C(=O)([O-])[O-].[K+].[K+].Cl[C:18]1[N:23]=[CH:22][N:21]=[C:20]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH:31]([CH:36](OC)[O:37][CH3:38])[C:32]([O:34][CH3:35])=[O:33])[CH:19]=1.[F-].[K+]>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][C:18]1[N:23]=[CH:22][N:21]=[C:20]([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2/[C:31](=[CH:36]\[O:37][CH3:38])/[C:32]([O:34][CH3:35])=[O:33])[CH:19]=1)#[N:3]

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 119072-Hydroxybenzonitrile2×HCID 522689Potassium FluorideHCID 5462222PotassiumHCID 110136152-(2-(6-Chloro-pyrimidin-4-yloxy)-phenyl)-3,3-dimethoxy-propionic acid methyl ester

Product 1

HCID 3034285Azoxystrobin

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropanoate in methylcyclohexane/chloromethoxypyrimidine (200.9 g, 59.91% strength) was vacuum distilled to leave the propanoate melt. A solution of the potassium salt of 2-cyanophenol was then prepared by mixing 2-cyanophenol (53.2 g) and potassium carbonate (81.2 g) in water (275 g). This solution was added to the methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3,3-dimethoxypropanoate melt, which had previously been cooled to 90° C. Potassium fluoride (15.9 g) and tetrabutylammonium bromide (21.5 g) was then added to the reaction solution. The resulting mixture was stirred at 105° C. for 23 hours. Any distillates were allowed to come off under atmospheric conditions. (E)-methyl 2-[2-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate was produced (77.9 area %).

Sources & evidence

ORD record
ord-d4e3b4e2c335411aa494a40a9625361e
Source dataset
uspto-grants-2000_11
Patent number
US06153750

Reaction notes

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