Water → HCID 14074439, compound

HRID 975221Notes

Reaction equation

HRID 975221 reaction equation
[F:1][C:2]([F:19])([F:18])[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:6]=1)[OH:4].Cl[O-].[Na+].O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[O:11]([C:7]1[N:6]=[C:5]([C:3](=[O:4])[C:2]([F:19])([F:1])[F:18])[CH:10]=[CH:9][CH:8]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 962WaterHCID 15592688HCID 15592688, compoundHCID 23665760Sodium Hypochlorite

Product 1

HCID 14074439HCID 14074439, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

9.38 g (0.035 mol) of 2,2,2-trifluoro-1-(6-phenoxy-2-pyridyl)ethanol and 0.58 g (0.0017 mol) of tetrabutylammonium hydrogen sulfate are dissolved in 200 ml of methylene chloride at room temperature. 22 ml (0.042 mol) of an approximately 12% strength sodium hypochlorite solution are metered in within 15 minutes with vigorous stirring and the mixture is stirred for a further 4 hours during which the reaction temperature rises to 30° C. The reaction mixture is added to 200 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 (0.4 mbar, 180° C. bath temperature), 4.75 g (50.6% of theory) of 6-phenoxy-2-trifluoroacetylpyridine are obtained. nD20 : 1.5298.

Workup

  1. customare metered in within 15 minutes
  2. stirringthe mixture is stirred for a further 4 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 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, 180° C. bath temperature), 4.75 g (50.6% of theory) of 6-phenoxy-2-trifluoroacetylpyridine
  10. customare obtained

Sources & evidence

ORD record
ord-58cfd87c455f493fa304bbc80d2a5d06
Source dataset
uspto-grants-1997_03
Patent number
US05608062

Reaction notes

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