Sodium Hypochlorite → HCID 86608017, compound

HRID 558618Notes

Reaction equation

HRID 558618 reaction equation
[CH2:1]([S:3][C:4](SCC)=[C:5]([C:19]([F:22])([F:21])[F:20])[CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)=[O:8])[CH3:2].[O-:26]Cl.[Na+]>C(O)(C(F)(F)F)=O.O>[CH2:1]([S:3][C:4](=[O:26])[CH:5]([C:19]([F:22])([F:21])[F:20])[CH2:6][C:7](=[O:8])[C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)[CH3:2]

Participants

5

Reactant 2

HCID 23665760Sodium HypochloriteHCID 866080184,4-Bis-ethylsulfanyl-3-trifluoromethyl-1-(4-trifluoromethyl-phenyl)-but-3-en-1-one

Product 1

HCID 86608017HCID 86608017, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 4,4-bis-ethylsulfanyl-3-trifluoromethyl-1-(4-trifluoromethyl-phenyl)-but-3-en-1-one (example C.26 step 3) (36.96 g, 92 mmol) in TFA (54.3 mL) and water (5.8 mL) was refluxed for 18 h under nitrogen atmosphere, the exhaust of the reaction was passed through a NaOCl solution to trap the liberated ethyl mercaptane. The volatiles were evaporated and the mixture was diluted with water and extracted with TBME, the organic layer was washed with sat. NaHCO3-sol. and brine, dried over Na2SO4. Removal of the solvent in vacuum left the title compound as a brown oil (31.2 g, 95%), which was used without further purification [according to J. Fluorine Chem. 2001, 107, 281.]. MS (EI) 339.0 [(M−F)+].

Workup

  1. temperaturewas refluxed for 18 h under nitrogen atmosphere
  2. customThe volatiles were evaporated
  3. additionthe mixture was diluted with water
  4. extractionextracted with TBME
  5. washthe organic layer was washed with sat. NaHCO3-sol
  6. dry with materialand brine, dried over Na2SO4
  7. customRemoval of the solvent in vacuum
  8. waitleft the title compound as a brown oil (31.2 g, 95%), which
  9. customwas used without further purification [according to J. Fluorine Chem. 2001, 107, 281.]

Sources & evidence

ORD record
ord-72ccc341ff3d4f3ba082d56d125191ec
Source dataset
uspto-grants-2011_11
Patent number
US08063048B2

Reaction notes

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