Dimethylformamide → 5-Bromo-2-(4-fluorophenoxy)pyridine

HRID 1891724Notes

Reaction equation

HRID 1891724 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][N:11]=1.CN(C)C=O.[H-].[Na+]>O>[Br:16][C:13]1[CH:14]=[CH:15][C:10]([O:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[N:11][CH:12]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 97324-FluorophenolHCID 24758Sodium hydrideHCID 693532,5-Dibromopyridine

Product 1

HCID 574253025-Bromo-2-(4-fluorophenoxy)pyridineYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-fluorophenol (2.1 g, 19 mmol), 2,5-dibromopyridine (3.0 g, 13 mmol) and N,N-dimethylformamide (30 mL) was added sodium hydride (730 mg, 15 mmol, 50% in oil) at 0° C., which was stirred for 10 minutes at room temperature. The reaction mixture was then stirred for 5 hours at 110° C. The reaction mixture was cooled to room temperature and water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water twice, and then washed with saturated aqueous sodium chloride, and was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=15:1) to obtain the title compound (2.6 g, 75%).

Workup

  1. stirringThe reaction mixture was then stirred for 5 hours at 110° C
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water twice
  5. washwashed with saturated aqueous sodium chloride
  6. concentrationwas concentrated under a reduced pressure
  7. customthe residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=15:1)

Sources & evidence

ORD record
ord-b68fe12bc55b4ad9bdb13aa3d8a9b86a
Source dataset
uspto-grants-2013_08
Patent number
US08507530B2

Reaction notes

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