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

HRID 407851Notes

Reaction equation

HRID 407851 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-dione

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.

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-dcd92fed86344e42b50e54d27456651d
Source dataset
uspto-grants-2014_06
Patent number
US08754242B2

Reaction notes

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