5-(5-Bromo-4-ethylphenyl)-4-hydroxycyclopent-2-enone → 2-(5-Bromo-2-ethylphenyl)cyclopent-4-ene-1,3-dione

HRID 339465Notes

Reaction equation

HRID 339465 reaction equation
[CH3:1][C:2](C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[Br:14][C:15]1[C:16](CC)=[CH:17][CH:18]=[C:19]([CH:21]2[C:25](=[O:26])[CH:24]=[CH:23][CH:22]2[OH:27])[CH:20]=1>CC(C)=O>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:1][CH3:2])=[C:19]([CH:21]2[C:22](=[O:27])[CH:23]=[CH:24][C:25]2=[O:26])[CH:20]=1

Participants

4

Reactant 2

HCID 666778065-(5-Bromo-4-ethylphenyl)-4-hydroxycyclopent-2-enoneHCID 131709961Jones' reagent

Product 1

HCID 580614862-(5-Bromo-2-ethylphenyl)cyclopent-4-ene-1,3-dioneYield 98.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Jones' reagent (75 ml of 1.67 M solution, 125 mmol) is added dropwise over 30 minutes to a cooled (ice-bath) solution of 5-(5-bromo-4-ethylphenyl)-4-hydroxycyclopent-2-enone (33 g, 117 mmol) in acetone (400 ml). The mixture is stirred for 20 minutes, then the cooling bath is removed and the mixture is stirred for 1 hour at room temperature. Isopropanol (150 ml) is added to the yellow slurry and the mixture is stirred at room temperature for 2 hours. The mixture is diluted with ethyl acetate and washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure to give 2-(5-bromo-2-ethylphenyl)cyclopent-4-ene-1,3-dione (32.17 g).

Workup

  1. customthe cooling bath is removed
  2. stirringthe mixture is stirred for 1 hour at room temperature
  3. additionIsopropanol (150 ml) is added to the yellow slurry
  4. stirringthe mixture is stirred at room temperature for 2 hours
  5. additionThe mixture is diluted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-473df9ca6690402d8946f8a093e69abd
Source dataset
uspto-grants-2014_11
Patent number
US08895474B2

Reaction notes

Loading…