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Water → 2-Phenoxy-4-trifluoroacetylfluorobenzene

HRID 975217
Notes
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Reaction equation

HRID 975217 reaction equation
[F:1][C:2]([F:20])([F:19])[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=1)[OH:4].Cl[O-].[Na+].O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[O:12]([C:7]1[CH:6]=[C:5]([C:3](=[O:4])[C:2]([F:1])([F:19])[F:20])[CH:10]=[CH:9][C:8]=1[F:11])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 962WaterHCID 19971591HCID 19971591, compoundHCID 23665760Sodium Hypochlorite

Product 1

HCID 199715862-Phenoxy-4-trifluoroacetylfluorobenzene

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst
HCID 6344
Dichloromethane
Solvent

Procedure

14.37 g (0.05 mol) of 2,2,2-trifluoro-1-(4-fluoro-3-phenoxyphenyl)ethanol and 0.85 g (0.0025 mol) of tetrabutylammonium hydrogen sulfate are dissolved in 200 ml of methylene chloride at room temperature. 31 ml (0.06 mol) of an approximately 12% strength sodium hypochlorite solution are metered in within 20 minutes with vigorous stirring and the mixture is stirred for a further 6 hours at room temperature. 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 (0.2 mbar, 150°-165° C. bath temperature), 10.8 g (76% of theory) of 2-phenoxy-4-trifluoroacetylfluorobenzene are obtained. nD20 : 1.5230.

Workup

  1. customare metered in within 20 minutes
  2. stirringthe mixture is stirred for a further 6 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 (0.2 mbar, 150°-165° C. bath temperature), 10.8 g (76% of theory) of 2-phenoxy-4-trifluoroacetylfluorobenzene
  9. customare obtained

Sources & evidence

ORD record
ord-b40a74212fbe442891043a75d060a2d9
Source dataset
uspto-grants-1997_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05608062

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes