Potassium Carbonate → 4-(3-bromophenyl)butan-2-one

HRID 517538Notes

Reaction equation

HRID 517538 reaction equation
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=O)[CH3:5].C([O-])([O-])=O.[K+].[K+].[Br:14][C:15]1[CH:20]=C[CH:18]=[C:17](CCl)[CH:16]=1>CCO>[Br:14][C:15]1[CH:20]=[C:5]([CH2:4][CH2:3][C:2](=[O:7])[CH3:1])[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31261AcetylacetoneHCID 5230591-Bromo-3-(chloromethyl)benzene

Product 1

HCID 2604364-(3-bromophenyl)butan-2-oneYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred mixture of pentane-2,4-dione (2.7 g, 26.7 mmol) and K2CO3 (3.4 g, 24.3 mmol) in EtOH (50 mL), 1-bromo-3-(chloromethyl)benzene (5.0 g, 24.3 mmol) was added at RT and the reaction mixture was refluxed overnight. After removal of volatiles under reduced pressure, the residue was taken up in EtOAc (100 mL) and washed with H2O (50 mL). The organic layer was separated, washed with brine, dried over Na2SO4, filtered and concentrated to afford the crude product, which was purified by silica gel column chromatography (EtOAc:Petroleum ether=1:10) to afford 4-(3-bromophenyl)butan-2-one as a colorless oil (3.7 g, 67%). MS (ES+) C10H11BrO requires: 226, 228 found: 227[M+H]+, 229 [M+2+H]+(1:1).

Workup

  1. additionwas added at RT
  2. temperaturethe reaction mixture was refluxed overnight
  3. customAfter removal of volatiles under reduced pressure
  4. washwashed with H2O (50 mL)
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto afford the crude product, which
  11. customwas purified by silica gel column chromatography (EtOAc:Petroleum ether=1:10)

Sources & evidence

ORD record
ord-1553231523bf4c398fe201334ebfd984
Source dataset
uspto-grants-2015_08
Patent number
US09115120B2

Reaction notes

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