3'-Bromoacetophenone → HCID 42545073, compound

HRID 881974Notes

Reaction equation

HRID 881974 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.C(O[CH:14](OCC)[N:15]([CH3:17])[CH3:16])C>CCO>[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])/[CH:9]=[CH:14]\[N:15]([CH3:17])[CH3:16])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 165023'-BromoacetophenoneHCID 70913Dimethylformamide diethylacetal

Product 1

HCID 42545073HCID 42545073, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 1-(3-bromophenyl)ethanone (4 g, 20 mmol) in EtOH (60 ml), was added at room temperature N,N-Dimethylformamide diethylacetal (7.15 g, 60 mmol) and the mixture was stirred at reflux temperature for 2 hours. After cooling to ambient temperature, the mixture was concentrated under reduced pressure. The residue was purified using normal phase chromatography, eluting with petroleum ether containing 50% ethyl acetate to give (Z)-1-(3-bromophenyl)-3-(dimethylamino)prop-2-en-1-one (3.0 g) as an oil.

Workup

  1. temperatureat reflux temperature for 2 hours
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customThe residue was purified
  4. washeluting with petroleum ether containing 50% ethyl acetate

Sources & evidence

ORD record
ord-43416091cff146799e8cd584ff6932a8
Source dataset
uspto-grants-2015_03
Patent number
US08993757B2

Reaction notes

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