Potassium Carbonate → Azoxystrobin

HRID 1859229Notes

Reaction equation

HRID 1859229 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9])#[N:2].C(=O)([O-])[O-].[K+].[K+].[F-].[K+].Cl[C:19]1[N:24]=[CH:23][N:22]=[C:21]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2/[C:32](=[CH:37]\[O:38][CH3:39])/[C:33]([O:35][CH3:36])=[O:34])[CH:20]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][C:19]1[N:24]=[CH:23][N:22]=[C:21]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2/[C:32](=[CH:37]\[O:38][CH3:39])/[C:33]([O:35][CH3:36])=[O:34])[CH:20]=1)#[N:2]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 119072-HydroxybenzonitrileHCID 522689Potassium FluorideHCID 11782200Methyl (2E)-2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyprop-2-enoate

Product 1

HCID 3034285Azoxystrobin

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
92.5 °C

Procedure

A mixture of 2-cyanophenol (41.0 g), potassium carbonate (62.1 g), potassium fluoride (12.3 g), tetrabutylammonium bromide (17.1 g), (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (98.9 g) and water (210 g) was heated at 90-95° C. for 22 hours. The reaction mixture was mixed with toluene and a further quantity of water. The organic layer was then separated. Toluene was removed from the organic phase by vacuum distillation (100° C., 20 mmHg). The melt was cooled to 85° C. after which methanol (120 ml) was added to help cooling to 70° C. The resulting mixture was cooled to 40° C. and kept at this temperature for 1 hour. It was then further cooled to 0-5° C. and held for another 1 hour period. The mixture was filtered to leave (E)-methyl 2-[2-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)pheny]-3-methoxypropenoate as the residue (85.5% isolated yield).

Workup

  1. customThe organic layer was then separated
  2. customToluene was removed from the organic phase by vacuum distillation (100° C., 20 mmHg)
  3. temperatureThe melt was cooled to 85° C. after which methanol (120 ml)
  4. additionwas added
  5. temperatureto help cooling to 70° C
  6. temperatureThe resulting mixture was cooled to 40° C.
  7. temperatureIt was then further cooled to 0-5° C.
  8. waitheld for another 1 hour period
  9. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-f635af08a42040da9ad7e950d435d12f
Source dataset
uspto-grants-2000_11
Patent number
US06153750

Reaction notes

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