1-(5-Bromo-2-fluorophenyl)ethanol → 1-(5-Bromo-2-fluorophenyl)ethanone

HRID 643343Notes

Reaction equation

HRID 643343 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:8]([OH:10])[CH3:9])[CH:7]=1>O1CCOCC1.[O-2].[O-2].[Mn+4]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1

Participants

4

Reactant 1

HCID 441820551-(5-Bromo-2-fluorophenyl)ethanol

Product 1

HCID 226074761-(5-Bromo-2-fluorophenyl)ethanoneYield 92.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1-(5-Bromo-2-fluoro-phenyl)-ethanol 102 (105 g, 0.479 mol) in dioxane (2 L) was added manganese dioxide (203 g, 2.35 mol). The reaction mixture was heated under reflux for 5 hours. The reaction mixture was allowed to cool to room temperature. The reaction mixture was filtered through Celite and the solid was washed with ether (1 L). The combined filtrate was evaporated under reduced pressure to afford the 1-(5-Bromo-2-fluoro-phenyl)-ethanone 103 (95.7 g, 0.441 mol) which was used in the next step without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 5 hours
  3. filtrationThe reaction mixture was filtered through Celite
  4. washthe solid was washed with ether (1 L)
  5. customThe combined filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-98b69f5c9b2f43afaa1eeb80b889744a
Source dataset
uspto-grants-2010_04
Patent number
US07700601B2

Reaction notes

Loading…