Water → 4-Chloro-2-fluoro-1-(2,2,2-trifluoroethoxy)benzene

HRID 1261148

Reaktionsgleichung

Reaktionsgleichung von HRID 1261148
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1.[F-].[K+].[F:12][C:13]([F:17])([F:16])[CH2:14]I.O>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:14][C:13]([F:17])([F:16])[F:12])=[C:4]([F:9])[CH:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 1819754-Chloro-2-fluorophenolHCID 522689Potassium Fluoride

Produkt 1

HCID 595067484-Chloro-2-fluoro-1-(2,2,2-trifluoroethoxy)benzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To 4-Chloro-2-fluoro-phenol (521, 5.0 g, 0.034 mol) in methanol (50.0 mL) was added potassium fluoride (2.2 g, 0.038 mol). The solvent was removed. The resulting salt was added to N,N-dimethylformaldehyde (25 mL), followed by adding 1,1,1-trifluoro-2-iodo-ethane (8.60 g, 40.9 mmol). The reaction was stirred at 50° C. overnight. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to give colorless oil (522, 2.0 g, 26%).

Aufarbeitung

  1. customThe solvent was removed
  2. additionThe resulting salt was added to N,N-dimethylformaldehyde (25 mL)
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. custompurified by silica gel column chromatography
  8. washeluting with 20% ethyl acetate in hexane
  9. customto give colorless oil (522, 2.0 g, 26%)

Quellen und Nachweise

ORD-Eintrag
ord-9f8d47da56a4470ea1624567d4c59c22
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470818B2

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