Dimethylformamide → 5-Bromo-2-(4-fluoro-benzyloxy)-pyridine

HRID 77938

Reaktionsgleichung

Reaktionsgleichung von HRID 77938
CN(C)C=O.[F:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][OH:12])=[CH:9][CH:8]=1.[H-].[Na+].Br[C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][N:19]=1>O>[Br:24][C:21]1[CH:22]=[CH:23][C:18]([O:12][CH2:11][C:10]2[CH:13]=[CH:14][C:7]([F:6])=[CH:8][CH:9]=2)=[N:19][CH:20]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 680224-Fluorobenzylic alcoholHCID 693532,5-Dibromopyridine

Produkt 1

HCID 592555025-Bromo-2-(4-fluoro-benzyloxy)-pyridineAusbeute 89,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To an N,N-dimethylformamide (30.0 mL) solution of 4-fluorobenzyl alcohol (2.60 g, 20.6 mmol) was added sodium hydride (0.88 g, 22.2 mmol, 60% in oil) under nitrogen atmosphere at 0° C., which was stirred for 10 minutes at room temperature. Next, 2,5-dibromopyridine (3.50 g, 14.8 mmol) was added at 0° C., and stirred for 19 hours at room temperature. Water was added to the reaction solution at room temperature, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:5) to obtain the title compound (3.75 g, 89.8%).

Aufarbeitung

  1. stirringstirred for 19 hours at room temperature
  2. extractionwhich was then extracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium chloride
  4. customthe solvent was evaporated under a reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:5)

Quellen und Nachweise

ORD-Eintrag
ord-bf50a301d30048e98b1961f991426d02
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841327B2

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