1-(2-Fluoro-4-iodo-phenyl)-ethanol → 2'-Fluoro-4'-iodoacetophenone

HRID 561962Notes

Reaction equation

HRID 561962 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[CH:9]([OH:11])[CH3:10]>ClCCl.[O-2].[O-2].[Mn+4]>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10]

Participants

4

Reactant 1

HCID 534154531-(2-Fluoro-4-iodo-phenyl)-ethanol

Product 1

HCID 534154542'-Fluoro-4'-iodoacetophenoneYield 91.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2-fluoro-4-iodo-phenyl)-ethanol (15.50 g, 58.26 mmol) in dichloromethane (250 mL) was added manganese dioxide (101.26 g, 1.17 mole) and the reaction mixture was heated to reflux for 24 hours. The reaction mixture was cooled, filtered through a pad of celite coated with a thin layer of silica gel and concentrated in vacuo to give 1-(2-fluoro-4-iodo-phenyl)-ethanone (14.04 g, 91%).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 24 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered through a pad of celite coated with a thin layer of silica gel
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b0979d46b68d4c4dbb22e9005ec959b9
Source dataset
uspto-grants-2011_11
Patent number
US08063085B2

Reaction notes

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