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

HRID 975201Notes

Reaction equation

HRID 975201 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.S([O-])(O)(=O)=O.Cl[O-].[Na+].O>C1(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 4

HCID 962WaterHCID 61778Sulfate, hydrogenHCID 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 1

HCID 1140TolueneSolvent

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 tetrabutylammnonium hydrogen sulfate are dissolved in 25 ml of toluene at room temperature. 6.1 ml (0.012 mol) of an approximately 12% strength sodium hypochlorite solution are metered in within 5 minutes with vigorous stirring and the mixture is stirred for a further 2.5 hours during which the reaction temperature rises to 27° C. The reaction mixture is added to 50 ml of water, the phases are separated, the aqueous phase is extracted several times with toluene and the combined organic phases are washed with saturated aqueous sodium chloride solution. After drying the organic phases with sodium sulfate, the volatiles are distilled off. Following distillation of the crude product in a kugelrohr (0.4 mbar, 100°-115° C. bath temperature), 1.78 g (85% 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 2.5 hours during which the reaction temperature
  3. customrises to 27° C
  4. customthe phases are separated
  5. extractionthe aqueous phase is extracted several times with toluene
  6. washthe combined organic phases are washed with saturated aqueous sodium chloride solution
  7. dry with materialAfter drying the organic phases with sodium sulfate
  8. distillationthe volatiles are distilled off
  9. distillationdistillation of the crude product in a kugelrohr (0.4 mbar, 100°-115° C. bath temperature), 1.78 g (85% of theory) of 2-chloro-5-trifluoroacetylpyridine
  10. customare obtained

Sources & evidence

ORD record
ord-fbf77f784a1c4222b62f0bbaa0d061ef
Source dataset
uspto-grants-1997_03
Patent number
US05608062

Reaction notes

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