Water → HCID 58278769, Verbindung

HRID 85171

Reaktionsgleichung

Reaktionsgleichung von HRID 85171
Cl[CH2:2][C@H:3]1[CH2:7][O:6][C:5]([CH3:9])([CH3:8])[O:4]1.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:12]=1[C:18]([F:21])([F:20])[F:19].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:2][C@H:3]2[CH2:7][O:6][C:5]([CH3:9])([CH3:8])[O:4]2)=[CH:13][C:12]=1[C:18]([F:19])([F:20])[F:21]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2734443(R)-(+)-4-(Chloromethyl)-2,2-dimethyl-1,3-dioxolaneHCID 222773074-Bromo-3-(trifluoromethyl)phenol

Produkt 1

HCID 58278769HCID 58278769, VerbindungAusbeute 56,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

(S)-4-(Chloromethyl)-2,2-dimethyl-1,3-dioxolane (63; 3.3 g, 20.5 mmol) was added to a mixture containing 4-bromo-3-(trifluoromethyl)phenol (126; 5 g, 20 mmol) and K2CO3 (8.30 g, 60 mmol) in 20 mL of DMF. The resulting reaction mixture was stirred at 60° C. for 6 h. Upon cooling to room temperature, the mixture was poured into water and extracted by EtOAc. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography (petroleum ether:EtOAc=50:1) to afford (S)-4-((4-bromo-3-(trifluoromethyl)phenoxy)methyl)-2,2-dimethyl-1,3-dioxolane (4 g, 56%).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. temperatureUpon cooling to room temperature
  3. extractionextracted by EtOAc
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by chromatography (petroleum ether:EtOAc=50:1)

Quellen und Nachweise

ORD-Eintrag
ord-99307bbd987049a580407d3592273530
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846947B2

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