Dimethylformamide → 2-(4-Bromo-benzyloxy)4-methyl-pyridine

HRID 1691003

Reaktionsgleichung

Reaktionsgleichung von HRID 1691003
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.CN(C)C=O.[H-].[Na+].F[C:18]1[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][N:19]=1>O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:7][C:18]2[CH:23]=[C:22]([CH3:24])[CH:21]=[CH:20][N:19]=2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 701194-Bromobenzyl alcoholHCID 27374032-Fluoro-4-methylpyridine

Produkt 1

HCID 592552882-(4-Bromo-benzyloxy)4-methyl-pyridineAusbeute 58,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a mixture of 4-bromobenzyl alcohol (4.54 g, 24.3 mmol) and N,N-dimethylformamide (50.0 mL) were added sodium hydride (1.00 g, 25.0 mmol, 60% in oil) was added at 0° C. under nitrogen atmosphere, which was stirred for 50 minutes at room temperature. 2-Fluoro-4-methylpyridine (1.80 g, 16.2 mmol) was then added thereto at 0° C., and stirred for 2 hours and 30 minutes at room temperature. Water was added to the reaction solution at room temperature, which was then extracted with ethyl acetate. The organic layer was separated, washed with saturated aqueous sodium chloride, and filtered. The filtrate was evaporated under a reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:15) to obtain the title compound (2.65 g, 58.8%).

Aufarbeitung

  1. additionwas added at 0° C. under nitrogen atmosphere
  2. stirringat 0° C., and stirred for 2 hours and 30 minutes at room temperature
  3. extractionwhich was then extracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with saturated aqueous sodium chloride
  6. filtrationfiltered
  7. customThe filtrate was evaporated under a reduced pressure
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:15)

Quellen und Nachweise

ORD-Eintrag
ord-ccbe8ed238f54e04a46fbd32d98f5545
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153662B2

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