Phenacyl bromide → 2-(4-Bromoanilino)-1-phenyl-1-ethanone

HRID 432334Notes

Reaction equation

HRID 432334 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.Br[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:12]>CN(C)C=O>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH2:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 78074-Bromoaniline

Product 1

HCID 8044422-(4-Bromoanilino)-1-phenyl-1-ethanoneYield 80.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution containing 4-bromoaniline (7.42 g, 0.0431 mol) and 2-bromoacetophenone (8.58 g, 0.0431 mol) in N,N-dimethylformamide (200 mL) N,N-diisopropylethylamine was added dropwise and the reaction mixture was stirred at ambient temperature for five hours. The solvent was removed under reduced pressure and the residue partitioned between dichloromethane (150 mL) and water (100 mL). The organic phase was dried with magnesium sulfate and concentrated under reduced pressure. The residue was suspended in diethyl ether and the precipitate was collected by filtration and dried to yield 2-(4-bromoanilino)-1-phenyl-1-ethanone (10.03 g, 0.0346 mol) as an off-white solid.

Workup

  1. additionwas added dropwise
  2. customThe solvent was removed under reduced pressure
  3. customthe residue partitioned between dichloromethane (150 mL) and water (100 mL)
  4. dry with materialThe organic phase was dried with magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. filtrationthe precipitate was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-0574f08883e34842925cd873f7fdf159
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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