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

HRID 1693851Notes

Reaction equation

HRID 1693851 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 592552882-(4-Bromo-benzyloxy)4-methyl-pyridineYield 58.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-a1aee3c0397d44568ad505cd2bb24f75
Source dataset
uspto-grants-2012_04
Patent number
US08158657B2

Reaction notes

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