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

HRID 490088Notes

Reaction equation

HRID 490088 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

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 (i.e., diatomaceous earth) 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 (i.e., diatomaceous earth)
  4. washthe solid was washed with ether (1 L)
  5. customThe combined filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-bdd85ab70f194254afbddf83ff28da8c
Source dataset
uspto-grants-2009_05
Patent number
US07528132B2

Reaction notes

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