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

HRID 1691045Notes

Reaction equation

HRID 1691045 reaction equation
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

Participants

6

Reactant 4

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

Product 1

HCID 592555025-Bromo-2-(4-fluoro-benzyloxy)-pyridineYield 89.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-13b5f762b4dc4e6e9ef54209b4cf2820
Source dataset
uspto-grants-2012_04
Patent number
US08153662B2

Reaction notes

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