Dimethylformamide → 5-(Benzyloxy)-2-chloropyridine

HRID 335162

Reaktionsgleichung

Reaktionsgleichung von HRID 335162
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH2:10]([O:8][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[N:7][CH:6]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 8198212-Chloro-5-hydroxypyridine

Produkt 1

HCID 100137175-(Benzyloxy)-2-chloropyridineAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

6-Chloropyridin-3-ol (30.00 g, 231.6 mmol), 1-(bromomethyl)benzene (43.57 g, 254.7 mmol), and potassium carbonate (80.01 g, 579.0 mmol) were added to DMF (500 mL) and stirred at ambient temperature overnight. Water was added and extracted with ether. The organic phase was washed with 1M NaOH, dried, filtered, and concentrated to provide the title compound (50.8 g, 99.86% yield).

Aufarbeitung

  1. extractionextracted with ether
  2. washThe organic phase was washed with 1M NaOH
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-cf8d630a2c4040d8bce771347a161879
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883828B2

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