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

HRID 78003

Reaction equation

HRID 78003 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].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:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])=[N:11][CH:12]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 97072-FluorophenolHCID 24758Sodium hydrideHCID 693532,5-Dibromopyridine

Product 1

HCID 592552115-Bromo-2-(2-fluorophenoxy)pyridineYield 28%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2-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, followed by extraction with ethyl acetate. The organic layer was washed twice with water and then washed with saturated aqueous sodium chloride, was concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=15:1) to obtain the title compound (940 mg, 28%).

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 twice with water
  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-eb787e56912f454bb24363cbda283138
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Linked notes

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