2,7-Dibromofluorene → 2,7Dibromofluorenone

HRID 393124Notes

Reaction equation

HRID 393124 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.[Mn]([O-])(=O)(=O)=[O:17].[K+]>O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2].O1CCCC1>[Br:1][C:2]1[C:3](=[O:17])[C:4]2[C:12](=[CH:13][CH:14]=1)[C:11]1[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=1)[CH:5]=2

Participants

5

Reactant 2

HCID 1400732,7-DibromofluoreneHCID 516875Potassium Permanganate

Product 1

HCID 534201032,7DibromofluorenoneYield 86%

Reagents, catalysts & solvents 2

HCID 24463Copper sulfate pentahydrateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
177.5 °C

Procedure

2,7-Dibromofluorene (20.00 g, 61.72 mmol), potassium permanganate (31.61 g, 200.0 mmol) and copper(II) sulphate pentahydrate (49.94 g, 200.0 mmol) were ground together to afford a fine powder. The powder was heated at 175-180° C. for 6 h. After cooling to room temperature, tetrahydrofuran (1 L) was added and the mixture was sonicated for 30 minutes before being filtered through celite. The solvent was removed under reduced pressure to afford a crude product, which was triturated with hot methanol (300 mL) and filtered before being dried under reduced pressure to afford 2,7-dibromofluorenone (1) (17.94 g, 86%) as a yellow solid, purity 100% (GC): 1H and 13C NMR spectra as expected; M+=338 (t).

Workup

  1. customto afford a fine powder
  2. temperatureAfter cooling to room temperature
  3. customthe mixture was sonicated for 30 minutes
  4. filtrationbefore being filtered through celite
  5. customThe solvent was removed under reduced pressure
  6. customto afford a crude product, which
  7. customwas triturated with hot methanol (300 mL)
  8. filtrationfiltered
  9. custombefore being dried under reduced pressure

Sources & evidence

ORD record
ord-f2c734279bd14489a425ef3bda0a21f2
Source dataset
uspto-grants-2004_10
Patent number
US06805922B2

Reaction notes

Loading…