2-Chlorophenol → Fluoxastrobin

HRID 716731

반응식

HRID 716731 반응식
[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]

참가 물질

9

반응물 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

생성물 1

HCID 11048796Fluoxastrobin수율 75%

시약·촉매·용매 4

HCID 887Methanol용매HCID 962Water용매HCID 1140Toluene용매HCID 6228Dimethylformamide용매

반응 조건

온도
55 °C

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-cba94f96e0f042a58794646ca7fd98d9
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193698B2

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