Acetamide, N-(3,5-dimethylphenyl)- → N-(4-bromo-3,5-dimethylphenyl)acetamide

HRID 1754935Notes

Reaction equation

HRID 1754935 reaction equation
[Br-:1].[Br-].[Br-].C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.[CH3:37][C:38]1[CH:39]=[C:40]([NH:45][C:46](=[O:48])[CH3:47])[CH:41]=[C:42]([CH3:44])[CH:43]=1>C(Cl)Cl.CO>[Br:1][C:43]1[C:42]([CH3:44])=[CH:41][C:40]([NH:45][C:46](=[O:48])[CH3:47])=[CH:39][C:38]=1[CH3:37]

Participants

4

Reactant 2

HCID 74903Acetamide, N-(3,5-dimethylphenyl)-HCID 53442637Benzyltrimethylammoniumtribromide

Product 1

HCID 4246250N-(4-bromo-3,5-dimethylphenyl)acetamideYield 90%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Benzyltrimethylammonium tribromide (BTMA-Br3) (7.8 g, 20.21 mmol) was added to a solution of N-(3,5-dimethyl-phenyl)-acetamide (3.0 g, 18.38 mmol) in CH2Cl2/MeOH (90 ml/90 ml) at room temperature in an Ar atmosphere. The reaction mixture was stirred at room temperature for 10 minutes. The reaction mixture was concentrated under reduced pressure, and CH2Cl2 was then added to the resulting residue. The organic layer was washed with H2O, and then dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:EtOAc=1:1) to give N-(4-bromo-3,5-dimethyl-phenyl)-acetamide (4.0 g, yield 90%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and CH2Cl2
  2. additionwas then added to the resulting residue
  3. washThe organic layer was washed with H2O
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:EtOAc=1:1)

Sources & evidence

ORD record
ord-377a7f6a6e6547a096434dc56397f3d7
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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