Potassium Carbonate → 1-Bromo-3,5-dichloro-2-(2,2-difluoroethoxy)benzene

HRID 1404552Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1404552
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[OH:10].C([O-])([O-])=O.[K+].[K+].[F:17][CH:18]([F:25])[CH2:19]OS(C)(=O)=O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[O:10][CH2:19][CH:18]([F:25])[F:17]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 206172-Bromo-4,6-dichlorophenolHCID 567764922,2-Difluoroethyl methanesulfonate

Produkt 1

HCID 441966871-Bromo-3,5-dichloro-2-(2,2-difluoroethoxy)benzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-bromo-4,6-dichloro-phenol (14.6 g, 60.3 mmol, Step A compound) in DMF (10 ml) were added K2CO3 (16.53 g, 120.6 mmol) and methanesulfonic acid 2,2-difluoro-ethyl ester (10.7 g, 66.4 mmol, Step B compound) and the mixture was heated to reflux for 16 h. The DMF was then evaporated in vacuo and the resulting residue was dissolved in EtOAc (300 ml). This solution was washed two times with water, with brine, dried with Na2SO4 and evaporated. The remaining crude product was purified by chromatography (silica gel; hexane) and the title compound was obtained as white solid (14.5 g, 79%). MS: m/z=304 [M]+.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 16 h
  3. customThe DMF was then evaporated in vacuo
  4. dissolutionthe resulting residue was dissolved in EtOAc (300 ml)
  5. washThis solution was washed two times with water
  6. dry with materialwith brine, dried with Na2SO4
  7. customevaporated
  8. customThe remaining crude product was purified by chromatography (silica gel; hexane)

Quellen und Nachweise

ORD-Eintrag
ord-e1732f944139462abea642e77db66850
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912221B2

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