Water → 1-(3-Bromo-4-fluorophenyl)-2,2,2-trifluoroethan-1-one

HRID 975213Notes

Reaction equation

HRID 975213 reaction equation
[F:1][C:2]([F:14])([F:13])[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]([Br:12])[CH:6]=1)[OH:4].Cl[O-].[Na+].O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[Br:12][C:7]1[CH:6]=[C:5]([C:3](=[O:4])[C:2]([F:13])([F:14])[F:1])[CH:10]=[CH:9][C:8]=1[F:11]

Participants

6

Reactant 3

HCID 962WaterHCID 199715901-(3-Bromo-4-fluorophenyl)-2,2,2-trifluoroethan-1-olHCID 23665760Sodium Hypochlorite

Product 1

HCID 199715881-(3-Bromo-4-fluorophenyl)-2,2,2-trifluoroethan-1-one

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

6.4 g (0.023 mol) of 2,2,2-trifluoro-1-(3-bromo-4-fluorophenyl)ethanol and 0.4 g (0.0012 mol) of tetrabutylammonium hydrogen sulfate are dissolved in 100 ml of methylene chloride at room temperature. 14.4 ml (0.028 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 27° C. The reaction mixture is added to 100 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 (0.5 mbar, 80°-100° C. bath temperature), 3.9 g (61.5% of theory) of 2-bromo-4-trifluoroacetylfluorobenzene are obtained. nD20 : 1.4905.

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 27° 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 (0.5 mbar, 80°-100° C. bath temperature), 3.9 g (61.5% of theory) of 2-bromo-4-trifluoroacetylfluorobenzene
  10. customare obtained

Sources & evidence

ORD record
ord-0ef165fda4e7470b90b1916438b2751d
Source dataset
uspto-grants-1997_03
Patent number
US05608062

Reaction notes

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