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

HRID 1891619Notes

Reaction equation

HRID 1891619 reaction equation
CN(C)C=O.[Br:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][OH:12])=[CH:9][CH:8]=1.[H-].[Na+].F[C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][N:19]=1>O>[Br:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][O:12][C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][N:19]=2)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 701194-Bromobenzyl alcoholHCID 27746352-Fluoro-5-methylpyridine

Product 1

HCID 592554492-(4-Bromo-benzyloxy)-5-methyl-pyridineYield 59.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an N,N-dimethylformamide (50.0 mL) solution of 4-bromobenzyl alcohol (4.54 g, 24.3 mmol) was added sodium hydride (1.00 g, 25.0 mmol, 60% in oil) under nitrogen atmosphere at 0° C., which was stirred for 30 minutes at room temperature. 2-Fluoro-5-methylpyridine (1.80 g, 16.2 mmol) was then added at 0° C., and stirred for 5 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 separated and 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=1:15) to obtain the title compound (2.67 g, 59.3%).

Workup

  1. stirringstirred for 5 hours at room temperature
  2. extractionwhich was then extracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous sodium chloride
  5. customthe solvent was evaporated under a reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:15)

Sources & evidence

ORD record
ord-78a8c11f7afb4dbdb90432059899649e
Source dataset
uspto-grants-2013_08
Patent number
US08507530B2

Reaction notes

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