2-Chlorophenol → Fluoxastrobin

HRID 716731

Reaction equation

HRID 716731 reaction equation
[CH3:1][O:2]/[N:3]=[C:4](\[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][C:18]1[C:23]([F:24])=[C:22](Cl)[N:21]=[CH:20][N:19]=1)/[C:5]1[O:10][CH2:9][CH2:8][O:7][N:6]=1.[Cl:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[OH:33].C([O-])([O-])=O.[K+].[K+].[OH-].[Na+]>C1(C)C=CC=CC=1.CO.O.CN(C=O)C>[CH3:1][O:2]/[N:3]=[C:4](/[C:5]1[O:10][CH2:9][CH2:8][O:7][N:6]=1)\[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][C:18]1[N:19]=[CH:20][N:21]=[C:22]([O:33][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[Cl:26])[C:23]=1[F:24]

Participants

9

Reactant 4

HCID 72452-ChlorophenolHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 59942128(Z)-(2-((6-chloro-5-fluoropyrimidin-4-yl)oxy)phenyl)(5,6-dihydro-1,4,2-dioxazin-3-yl)methanone O-methyl oxime

Product 1

HCID 11048796FluoxastrobinYield 75%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of (E)-(2-((6-chloro-5-fluoropyrimidin-4-yl)oxy)phenyl)(5,6-dihydro-1,4,2-dioxazin-3-yl)methanone O-methyl oxime (14)(100 g, 0.564 mol) in toluene was added 2-chlorophenol (54 g, 0.846 mol), K2CO3 (50 g, 0.733 mol), and DMF (50 mL) at ambient temperature. The reaction mixture was stirred at 50-60° C. for 3-4 h. The progress of the reaction was monitored by the HPLC analysis. Upon completion of the reaction, aqueous NaOH (10%) (200 mL) was charged followed by water (300 mL). The mixture was stirred and the toluene layer was separated. The toluene layer was washed with a solution of brine (600 mL). The final toluene layer was recovered completely to get the crude product. To the above crude product, methanol was charged and heated to 60° C. until the clear solution is formed. The solution was stirred at room temperature to get the pure product precipitated. The pure fluoxastrobin product was filtered and washed with methanol. The product was further dried to obtain the pure fluoxastrobin product meeting the desired specifications. Yield—75-88%.

Workup

  1. additionwas charged
  2. stirringThe mixture was stirred
  3. customthe toluene layer was separated
  4. washThe toluene layer was washed with a solution of brine (600 mL)
  5. customThe final toluene layer was recovered completely
  6. customto get the crude product
  7. temperatureheated to 60° C. until the clear solution
  8. customis formed
  9. stirringThe solution was stirred at room temperature
  10. customto get the pure product
  11. customprecipitated
  12. filtrationThe pure fluoxastrobin product was filtered
  13. washwashed with methanol
  14. customThe product was further dried

Sources & evidence

ORD record
ord-cba94f96e0f042a58794646ca7fd98d9
Source dataset
uspto-grants-2015_11
Patent number
US09193698B2

Linked notes

Loading…