3-Hydroxypyridine → 3-(3-Fluoro-5-nitrophenoxy)pyridine

HRID 1809826Notes

Reaction equation

HRID 1809826 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[F:14][C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[C:17](F)[CH:16]=1>CN(C)C=O.[Cl-].[NH4+]>[F:14][C:15]1[CH:16]=[C:17]([CH:18]=[C:19]([N+:21]([O-:23])=[O:22])[CH:20]=1)[O:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 79713-HydroxypyridineHCID 11430Potassium CarbonateHCID 752721,3-Difluoro-5-nitrobenzene

Product 1

HCID 573536423-(3-Fluoro-5-nitrophenoxy)pyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-hydroxypyridine (3.25 g) in dimethylformamide (75 ml), 6.75 g of potassium carbonate and 5.0 g of 1,3-difluoro-5-nitrobenzene were added, and the reaction solution was stirred at 100° C. for 6 hours. The reaction solution was cooled, thereafter diluted with a saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The combined organic layers were washed with water and a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resultant residue was purified by silica gel chromatography to yield the title compound as a yellow oil.

Workup

  1. temperatureThe reaction solution was cooled
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with water
  4. dry with materiala saturated saline solution and dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resultant residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-454ad8dbb2aa47ba80ca71c34b9567e5
Source dataset
uspto-grants-2013_01
Patent number
US08362052B2

Reaction notes

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