Water → 1-(6-Chloropyridin-3-yl)-2,2,2-trifluoroethanone

HRID 975200Notes

Reaction equation

HRID 975200 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:13])[C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.Cl[O-].[Na+].O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[C:9]([F:11])([F:12])[F:10])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 199715811-(6-Chloropyridin-3-yl)-2,2,2-trifluoroethan-1-olHCID 23665760Sodium Hypochlorite

Product 1

HCID 199715831-(6-Chloropyridin-3-yl)-2,2,2-trifluoroethanone

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 7237O-XyleneSolvent

Procedure

2.11 g (0.01 mol) of 2-chloro-5-(2,2,2-trifluoro-1-hydroxyethyl)pyridine and 0.18 g (0.0005 mol) of tetrabutylammonium hydrogen sulfate are dissolved in 30 ml of xylene at room temperature. 7.3 ml (0.012 mol) of an approximately 10% strength sodium hypochlorite solution are metered in within 5 minutes with vigorous stirring and the mixture is stirred for a further 2 hours during which the reaction temperature rises to 28° C. The reaction mixture is added to 50 ml of water, the phases are separated, the aqueous phase is extracted several times with xylene and the combined organic phases are washed with saturated aqueous sodium chloride solution. After drying the organic phase with sodium sulfate, the volatiles are distilled off. Following distillation of the crude product in a kugelrohr (0.4 mbar, 100°-110° C. bath temperature), 1.89 g (90% of theory) of 2-chloro-5-trifluoroacetylpyridine are obtained.

Workup

  1. customare metered in within 5 minutes
  2. stirringthe mixture is stirred for a further 2 hours during which the reaction temperature
  3. customrises to 28° C
  4. customthe phases are separated
  5. extractionthe aqueous phase is extracted several times with xylene
  6. washthe combined organic phases are washed with saturated aqueous sodium chloride solution
  7. dry with materialAfter drying the organic phase with sodium sulfate
  8. distillationthe volatiles are distilled off
  9. distillationdistillation of the crude product in a kugelrohr (0.4 mbar, 100°-110° C. bath temperature), 1.89 g (90% of theory) of 2-chloro-5-trifluoroacetylpyridine
  10. customare obtained

Sources & evidence

ORD record
ord-4f5013ca21404cbbba42d96b53ce8ffb
Source dataset
uspto-grants-1997_03
Patent number
US05608062

Reaction notes

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