1-(3-Bromo-2,6-difluorophenyl)ethanol → 1-(3-Bromo-2,6-difluorophenyl)ethanone

HRID 1497393Notes

Reaction equation

HRID 1497393 reaction equation
[Br:1][C:2]1[C:3]([F:12])=[C:4]([CH:9]([OH:11])[CH3:10])[C:5]([F:8])=[CH:6][CH:7]=1>C(#N)C.[O-2].[O-2].[Mn+4]>[Br:1][C:2]1[C:3]([F:12])=[C:4]([C:9](=[O:11])[CH3:10])[C:5]([F:8])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 681095541-(3-Bromo-2,6-difluorophenyl)ethanol

Product 1

HCID 681101191-(3-Bromo-2,6-difluorophenyl)ethanoneYield 89.8%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(3-bromo-2,6-difluorophenyl)ethanol (3.91 g) in acetonitrile (50 ml) was added manganese dioxide (2.87 g) at room temperature, and the mixture was heated under reflux for 20 hr. The reaction mixture was cooled, the insoluble material was filtered off, and the obtained filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (3.48 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 20 hr
  3. temperatureThe reaction mixture was cooled
  4. filtrationthe insoluble material was filtered off
  5. concentrationthe obtained filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d902384c84e44c5ea1640acfd0e966fa
Source dataset
uspto-grants-2015_12
Patent number
US09199963B2

Reaction notes

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