3,4-Dichlorophenol → 4-Methylphenyl 5-chloro-4-(3,4-dichlorophenoxy)-2-fluorobenzoate

HRID 2359279Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2359279
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].C(=O)([O-])[O-].[K+].[K+].[Cl:16][C:17]1[C:18](F)=[CH:19][C:20]([F:33])=[C:21]([CH:32]=1)[C:22]([O:24][C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1)=[O:23]>CS(C)=O.C(OCC)(=O)C>[Cl:16][C:17]1[C:18]([O:9][C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)=[CH:19][C:20]([F:33])=[C:21]([CH:32]=1)[C:22]([O:24][C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=1)=[O:23]

Komponenten

6

Edukt 3

HCID 72583,4-DichlorophenolHCID 11430Potassium CarbonateHCID 58042518HCID 58042518, Verbindung

Produkt 1

HCID 580463024-Methylphenyl 5-chloro-4-(3,4-dichlorophenoxy)-2-fluorobenzoateAusbeute 100,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3,4-Dichlorophenol (110 mg, 0.67 mmol) and potassium carbonate (20 mg, 1.42 mmol) were stirred in dimethylsulfoxide (20 mL). After 5 minutes, 4-methylphenyl 5-chloro-2,4-difluorobenzoate (Preparation 10, 200 mg, 0.71 mmol) was added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate and washed with a 1M aqueous solution of sodium hydroxide. The aqueous phase was extracted with ethyl acetate. The combined organic phase was dried over magnesium sulphate, filtered and concentrated in vacuo to give a white solid. The solid was purified by silica gel column chromatography (50% ethyl acetate in heptane elution) to afford the title compound as a white solid (286 mg, 95%).

Aufarbeitung

  1. washwashed with a 1M aqueous solution of sodium hydroxide
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. dry with materialThe combined organic phase was dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a white solid
  7. customThe solid was purified by silica gel column chromatography (50% ethyl acetate in heptane elution)

Quellen und Nachweise

ORD-Eintrag
ord-112a8016cea34f3caff23e7fa4339a30
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08685977B2

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