Ethyl Acetate → 2-Bromo-5-[[(4-fluorophenyl)thio](2,3,6-trifluorophenyl)methyl]-4-methylpyridine

HRID 1641699Notes

Reaction equation

HRID 1641699 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH:9](Cl)[C:10]2[C:15]([F:16])=[CH:14][CH:13]=[C:12]([F:17])[C:11]=2[F:18])=[CH:4][N:3]=1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([SH:27])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH:9]([S:27][C:24]2[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=2)[C:10]2[C:15]([F:16])=[CH:14][CH:13]=[C:12]([F:17])[C:11]=2[F:18])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 677894-FluorothiophenolHCID 866311512-Bromo-5-[chloro(2,3,6-trifluorophenyl)methyl]-4-methylpyridine

Product 1

HCID 577364302-Bromo-5-[[(4-fluorophenyl)thio](2,3,6-trifluorophenyl)methyl]-4-methylpyridineYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-bromo-5-[chloro(2,3,6-trifluorophenyl)methyl]-4-methylpyridine (4.65 g, 13.3 mmol) in N,N-dimethylformamide (70 ml), 4-fluorobenzenethiol (1.41 ml, 13.3 mmol) and then potassium carbonate (2.02 g, 14.6 mmol) were added in an argon atmosphere at 0° C., and the resulting mixture was stirred for 4 hours at room temperature. Ethyl acetate and water were added to the reaction mixture at 0° C., the organic layer was separated, and then the organic layer was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was subjected to flash silica gel chromatography. The fraction obtained from an elution with hexane:ethyl acetate=19:1 was concentrated under reduced pressure, and the resulting residue was washed with hexane, and then was collected by filtration, to obtain the title compound (5.17 g, 11.7 mmol, 88%) as a white solid.

Workup

  1. customthe organic layer was separated
  2. washthe organic layer was washed with saturated brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe fraction obtained from an elution with hexane
  7. concentrationethyl acetate=19:1 was concentrated under reduced pressure
  8. washthe resulting residue was washed with hexane
  9. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-d064fe5447a942fda8589001e2573e92
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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