Diethyl Sulfate → 3-Chloro-4-fluorophenetole

HRID 2095624Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2095624
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].[CH2:10](OS(OCC)(=O)=O)[CH3:11].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([O:9][CH2:10][CH3:11])[CH:5]=[CH:6][C:7]=1[F:8]

Komponenten

5

Edukt 3

HCID 6163Diethyl SulfateHCID 11430Potassium CarbonateHCID 757903-Chloro-4-fluorophenol

Produkt 1

HCID 27737033-Chloro-4-fluorophenetole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 3-chloro-4-fluorophenol (2.0 g, 13.7 mmol), diethylsulfate (1.58 mL, 17.8 mmol) and K2CO3 (9.4 g, 68.5 mmol) in acetone (20 mL) was heated under refluxed for 3 h. The reaction mixture was filtered and concentrated. The residue was diluted with ethyl acetate (50 mL), washed with water (30 mL) and brine. The organic layer was dried (Na2SO4) and concentrated to give the title compound as a liquid. 1H NMR (CDCl3, 400 MHz): δ=1.39 (t, 3H, J=7.2 Hz), 3.97 (q, 2H, J=7.2 Hz), 6.71-6.74 (m, 1H), 6.89-6.91 (m, 1H), 7.02 (t, 1H, J=8.8 Hz).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder refluxed for 3 h
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated
  5. additionThe residue was diluted with ethyl acetate (50 mL)
  6. washwashed with water (30 mL) and brine
  7. dry with materialThe organic layer was dried (Na2SO4)
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1d69fe330c7c483785a8c4dc4a4b67f5
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08445510B2

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