p-Aminoacetophenone → 1-(4-Amino-3-bromo-phenyl)-ethanone

HRID 1190201Notes

Reaction equation

HRID 1190201 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1)=[O:3].[Br:11]N1C(=O)CCC1=O>CC#N>[NH2:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH3:1])=[CH:5][C:6]=1[Br:11]

Participants

4

Reactant 2

HCID 7468p-AminoacetophenoneHCID 67184N-bromobutanimide

Product 1

HCID 15152811-(4-Amino-3-bromo-phenyl)-ethanoneYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 4-aminoacetophenone (5.67 g, 0.0419 mol) in 30 mL of CH3CN at 0° C. was added N-bromosuccinimide (7.83 g, 0.0439 mol) in 20 mL of CH3CN dropwise. The reaction was allowed to warm to room temperature and concentrated in vacuo after stirring 16 h. The crude residue was dissolved in EtOAc (100 mL), washed with saturated aqueous NaHCO3 (1×100 mL), brine (1×100 mL) and dried (Na2SO4). The solvent was removed under vacuum to afford the title compound (7.62 g, 85%) as a yellow solid. Mass spectrum (ESI, m/z): Calcd. for C8H8BrNO, 213.9 (M+H). found 214.0.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe crude residue was dissolved in EtOAc (100 mL)
  3. washwashed with saturated aqueous NaHCO3 (1×100 mL), brine (1×100 mL)
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-a35b3840c2a2426d8a057c3b0d258396
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

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