Water → HCID 19689334, compound

HRID 975210Notes

Reaction equation

HRID 975210 reaction equation
[F:1][C:2]([F:18])([F:17])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([OH:16])[C:12]([F:15])([F:14])[F:13])=[CH:7][N:6]=1.Cl[O-].[Na+].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClC1C=CC=CC=1>[F:18][C:2]([F:1])([F:17])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:16])[C:12]([F:13])([F:14])[F:15])=[CH:7][N:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 199715826-(2,2,2-Trifluoroethoxy)-α-(trifluoromethyl)-3-pyridinemethanolHCID 23665760Sodium Hypochlorite

Product 1

HCID 19689334HCID 19689334, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 7964ChlorobenzeneSolvent

Procedure

2.75 g (0.01 mol) of 2-(2,2,2-trifluoroethoxy)-5-(2,2,2-trifluoro-1-hydroxyethyl)pyridine and 0.17 g (0.0005 mol) of tetrabutylammonium bromide are dissolved in 30 ml of chlorobenzene 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 4 hours at room temperature. 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 chloride solution. After drying the organic phase with sodium sulfate, the volatiles are distilled off. Following distillation of the crude product in a kugelrohr (0.3 mbar, 100°-120° C. bath temperature), 0.68 g (24.7% of theory) of 2-(2,2,2-trifluoroethoxy)-5-trifluoroacetylpyridine are obtained.

Workup

  1. customare metered in within 5 minutes
  2. stirringthe mixture is stirred for a further 4 hours at room temperature
  3. customthe phases are separated
  4. extractionthe aqueous phase is extracted several times with methylene chloride
  5. washthe combined organic phases are washed with saturated aqueous sodium chloride solution
  6. dry with materialAfter drying the organic phase with sodium sulfate
  7. distillationthe volatiles are distilled off
  8. distillationdistillation of the crude product in a kugelrohr (0.3 mbar, 100°-120° C. bath temperature), 0.68 g (24.7% of theory) of 2-(2,2,2-trifluoroethoxy)-5-trifluoroacetylpyridine
  9. customare obtained

Sources & evidence

ORD record
ord-2c5e7e05f6a841f295e515d28f759c2c
Source dataset
uspto-grants-1997_03
Patent number
US05608062

Reaction notes

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