Pyridine → 4'-Bromoacetanilide

HRID 1665694Notes

Reaction equation

HRID 1665694 reaction equation
N1C=CC=CC=1.C(O[C:11](=[O:13])[CH3:12])(=O)C.[Br:14][C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1>C(Cl)Cl>[Br:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:11](=[O:13])[CH3:12])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 78074-BromoanilineHCID 7918Acetic Anhydride

Product 1

HCID 76834'-BromoacetanilideYield 72.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Pyridine (551 mg, 5.8 mmol) and acetic anhydride (650 mg, 0.6 mL, 6.4 mmol) were added to a cold solution (at 0° C.) of 4-bromo-phenylamine (1 g, 5.8 mmol) in DCM (10 mL) and stirring was continued at ambient temperature for 2 hrs. The reaction mixture was diluted with DCM and washed the organic layer with water followed by brine solution. The organic layer collected was dried over sodium sulfate and concentrated under reduced pressure to afford 900 mg (69.5% yield) of N-(4-bromo-phenyl)-acetamide.

Workup

  1. washwashed the organic layer with water
  2. customThe organic layer collected
  3. dry with materialwas dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b518c8d3285d487ca08e519bfc4e5ee4
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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