Water → HCID 55139361, compound

HRID 920305Notes

Reaction equation

HRID 920305 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[N:6][CH:7]=1.[F:9][C:10]1[CH:11]=[C:12]([OH:17])[CH:13]=[CH:14][C:15]=1[F:16].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][C:12]2[CH:13]=[CH:14][C:15]([F:16])=[C:10]([F:9])[CH:11]=2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 759273,4-DifluorophenolHCID 27831685-Bromo-2-fluoropyridine

Product 1

HCID 55139361HCID 55139361, compoundYield 61.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-bromo-2-fluoropyridine (19 g, 108 mmol) and 3,4-difluorophenol (14.05 g, 108 mmol) in dimethyl sulfoxide (DMSO) (150 mL) was added potassium carbonate (26.9 g, 194 mmol). The reaction mixture was stirred at 80° C. for 2 hr, then H2O (200 ml) and EtOAc (200 ml) were added. The organic layer was separated, and then concentrated under reduced pressure. The crude product was purified by a silica gel chromatography eluting with Hex/EtOAc (10:1) to provide 5-bromo-2-(3,4-difluorophenoxy)pyridine (19 g, 55.4%).

Workup

  1. customThe organic layer was separated
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product was purified by a silica gel chromatography
  4. washeluting with Hex/EtOAc (10:1)

Sources & evidence

ORD record
ord-d6411121040848b4bc069a60cdb0c863
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Reaction notes

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