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

HRID 975198Notes

Reaction equation

HRID 975198 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.C(Cl)Cl>[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 6344DichloromethaneSolvent

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 methylene chloride 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 30° C. The reaction mixture is added to 50 ml of water, the phases are separated, the aqueous phase is extracted several times with methylene chloride and the combined organic phases are washed with saturated aqueous sodium 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 (0.5 mbar, 100°-120° C. bath temperature), 1.13 g (54% of theory) of 2-chloro-5-trifluoroacetylpyridine are obtained, which, according to GC, is 99.8% pure. nD20 : 1.4887.

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 30° C
  4. customthe phases are separated
  5. extractionthe aqueous phase is extracted several times with methylene chloride
  6. washthe combined organic phases are washed with saturated aqueous sodium 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 (0.5 mbar, 100°-120° C. bath temperature), 1.13 g (54% of theory) of 2-chloro-5-trifluoroacetylpyridine
  10. customare obtained

Sources & evidence

ORD record
ord-34f514b91d7f419fb24978b23a2cfd36
Source dataset
uspto-grants-1997_03
Patent number
US05608062

Reaction notes

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