3-Methyl-2-butanone → 1-(4-Bromo-phenyl)-4-methyl-pent-1-en-3-one

HRID 853189Notes

Reaction equation

HRID 853189 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][CH:11]([CH3:15])[C:12](=[O:14])[CH3:13]>[OH-].[Na+].C(O)C.O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:13][C:12](=[O:14])[CH:11]([CH3:15])[CH3:10])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 112513-Methyl-2-butanoneHCID 707414-Bromobenzaldehyde

Product 1

HCID 3742501-(4-Bromo-phenyl)-4-methyl-pent-1-en-3-oneYield 58.1%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

4-Bromo-benzaldehyde (available from Aldrich, 10.0 g, 54.3 mmol) was added to a solution of 3-methyl-butan-2-one (available from Aldrich, 4.7 g, 54.7 mmol) in 10 mL of 10% NaOH(aq) and 20 mL of ethanol. After stirring at room temperature for 3 h, the reaction mixture was diluted with water (50 mL) and extracted with diethyl ether (3×20 mL). The organic layer was then washed with brine (1×5 mL), dried (MgSO4) and concentrated at reduced pressure. Purification by flash chromatography (95:5 hexane/ethyl acetate) yielded the title compound (7.98 g, 58% yield) as a light yellow oil:

Workup

  1. extractionextracted with diethyl ether (3×20 mL)
  2. washThe organic layer was then washed with brine (1×5 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated at reduced pressure
  5. customPurification by flash chromatography (95:5 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-001dcec6ce494233aead8ec292cd9027
Source dataset
uspto-grants-2007_08
Patent number
US07253319B2

Reaction notes

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