Potassium Carbonate → 2-Fluoro-6-(4-trifluoromethylphenoxy)pyridine

HRID 1266921Notes

Reaction equation

HRID 1266921 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21](F)[N:20]=1.S([O-])([O-])(=O)=O.[Mg+2]>CN(C=O)C.CCCCCC.O>[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:9][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:10])([F:11])[F:1])=[CH:8][CH:7]=2)[N:20]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 678744-(Trifluoromethyl)phenolHCID 739342,6-Difluoropyridine

Product 1

HCID 185447832-Fluoro-6-(4-trifluoromethylphenoxy)pyridineYield 60%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8058HexaneSolvent

Procedure

A reaction flask was loaded with 4-trifluoromethylphenol (8.4 g), anhydrous potassium carbonate (8.6 g), and DMF (15 ml), followed by stirring at room temperature for 15 minutes. To this mixture, 2,6-difluoropyridine (6.0 g) dissolved in DMF (15 ml) was dropwise added in one hour. Thereafter, the temperature was raised up to 60° C., and the mixture was stirred for six hours. Water was added to the reaction mixture, and extraction was carried out with hexane, followed by addition of magnesium sulfate to the extracted liquid for drying. After filtration to remove magnesium sulfate, hexane was removed by an evaporator to give 2-fluoro-6-(4-trifluoromethylphenoxy)-pyridine (8.0 g).

Workup

  1. additionwas dropwise added in one hour
  2. temperatureThereafter, the temperature was raised up to 60° C.
  3. stirringthe mixture was stirred for six hours
  4. customfor drying
  5. filtrationAfter filtration
  6. customto remove magnesium sulfate, hexane
  7. customwas removed by an evaporator

Sources & evidence

ORD record
ord-fe7a0e6e858046bdbafefd5e41082ec3
Source dataset
uspto-grants-2003_04
Patent number
US06551682B1

Reaction notes

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