Water → 1-(2,2-Dichloro-1,1-difluoroethoxy)-4-(4-(methylsulfonyl)phenoxy)benzene

HRID 2164643

Reaktionsgleichung

Reaktionsgleichung von HRID 2164643
[CH3:1][S:2]([C:5]1[CH:18]=[CH:17][C:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[OH-].[Na+].[F:21][C:22]([F:26])=[C:23]([Cl:25])[Cl:24].O>C(#N)C>[Cl:24][CH:23]([Cl:25])[C:22]([F:26])([F:21])[O:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][C:8]2[CH:17]=[CH:18][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=2)=[CH:11][CH:12]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 65921,1-Dichloro-2,2-difluoroetheneHCID 14798Sodium HydroxideHCID 514882Phenol, 4-(4-(methylsulfonyl)phenoxy)-

Produkt 1

HCID 130785191-(2,2-Dichloro-1,1-difluoroethoxy)-4-(4-(methylsulfonyl)phenoxy)benzeneAusbeute 89,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

To a solution of 5.29 g (0.0200 mole) of 4-(4-(methylsulfonyl)phenoxy)phenol (Example 21) in 100 ml of acetonitrile was added 0.80 g (0.0200 mole) of NaOH. The mixture was stirred at room temperature for 1 hr and then cooled to 3° C. in an ice bath. To the cold slurry was slowly added 4.0 g (0.0300 mole) of 1,1-difluoro-2,2-dichloroethylene dissolved in 15 ml of acetonitrile and the reaction mixture stirred at 3°-5° C. for 3 hrs. To the cold mixture 150 ml of water was added which resulted in the product precipitating as an oil. The product was extracted from the mixture with CH2Cl2. The organic layer was washed with water, dried (Na2SO4) and solvent removed in vacuo, which gave 7.1 g (89.4% yield) of product. Purification was accomplished by column chromatography using silica gel as the support and chloroform as the eluent, which afforded purified 1 -(2,2-dichloro-1,1-difluoroethoxy)-4-(4-(methylsulfonyl)phenoxy)benzene, mp 67°-70° C.

Aufarbeitung

  1. temperaturecooled to 3° C. in an ice bath
  2. stirringthe reaction mixture stirred at 3°-5° C. for 3 hrs
  3. customresulted in the product
  4. customprecipitating as an oil
  5. extractionThe product was extracted from the mixture with CH2Cl2
  6. washThe organic layer was washed with water
  7. dry with materialdried (Na2SO4) and solvent
  8. customremoved in vacuo, which

Quellen und Nachweise

ORD-Eintrag
ord-d14eb91a8c69406ab0fbbd650adcc03b
Quelldatensatz
uspto-grants-1985_03
Patentnummer
US04505929

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