3-(Trifluoromethyl)phenol → 3-Chloro-2-(3-(trifluoromethyl)phenoxy)pyridine

HRID 443009

Reaktionsgleichung

Reaktionsgleichung von HRID 443009
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.Cl[C:13]1[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][N:14]=1>CN(C)C=O>[Cl:19][C:18]1[C:13]([O:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=2)=[N:14][CH:15]=[CH:16][CH:17]=1

Komponenten

4

Edukt 2

HCID 73763-(Trifluoromethyl)phenolHCID 169882,3-Dichloropyridine

Produkt 1

HCID 180084773-Chloro-2-(3-(trifluoromethyl)phenoxy)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

7.68 g of sodium hydride dispersion (ca. 50 percent in mineral oil) was washed with pentane under nitrogen and 100 ml of N,N-dimethylformamide was then added. 21.92 g (135 mmol) of 3-(trifluoromethyl)phenol was added dropwise over 30 minutes at room temperature. The resulting phenate solution was added dropwise over 2 hours, under nitrogen, to a solution of 20.1 g (136 mmol) of 2,3-dichloropyridine in 80 ml of N,N-dimethylformamide, heated to 120° C. After 3 hours of reaction time, the mixture was cooled to room temperature, the sodium chloride which had precipitated out was filtered off and the filtrate was concentrated. The residue was extracted with toluene and 0.1N hydrochloric acid and the organic phase was washed with saturated sodium chloride solution and concentrated. The oily residue was distilled under vacuum. The yield was 24.75 g (67 percent) of a colorless oil, content (GC): 99.7 percent. Other data concerning the product was:

Aufarbeitung

  1. wash7.68 g of sodium hydride dispersion (ca. 50 percent in mineral oil) was washed with pentane under nitrogen
  2. addition100 ml of N,N-dimethylformamide was then added
  3. customAfter 3 hours of reaction time
  4. temperaturethe mixture was cooled to room temperature
  5. customthe sodium chloride which had precipitated out
  6. filtrationwas filtered off
  7. concentrationthe filtrate was concentrated
  8. extractionThe residue was extracted with toluene and 0.1N hydrochloric acid
  9. washthe organic phase was washed with saturated sodium chloride solution
  10. concentrationconcentrated
  11. distillationThe oily residue was distilled under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b1f797436a324e67b82cf4949508d8ad
Quelldatensatz
uspto-grants-1999_04
Patentnummer
US05892032

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