N-(4-acetyl-3,5-dimethylphenyl)acetamide → N-(4-(2-bromoacetyl)-3,5-dimethylphenyl)acetamide

HRID 1465608Notes

Reaction equation

HRID 1465608 reaction equation
[C:1]([C:4]1[C:9]([CH3:10])=[CH:8][C:7]([NH:11][C:12](=[O:14])[CH3:13])=[CH:6][C:5]=1[CH3:15])(=[O:3])[CH3:2].[Br-:16].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>C(#N)C>[Br:16][CH2:2][C:1]([C:4]1[C:5]([CH3:15])=[CH:6][C:7]([NH:11][C:12](=[O:14])[CH3:13])=[CH:8][C:9]=1[CH3:10])=[O:3]

Participants

4

Reactant 2

HCID 18788473N-(4-acetyl-3,5-dimethylphenyl)acetamideHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 18788447N-(4-(2-bromoacetyl)-3,5-dimethylphenyl)acetamideYield 101%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-(4-acetyl-3,5-dimethylphenyl)acetamide (5.00 g, 24.4 mmol) in acetonitrile (48.7 mL) was added tetrabutylammoniumtribromide (TBABr3, 11.7 g, 24.4 mmol). The reaction was stirred at room temperature overnight. The solution was concentrated under reduced pressure, added with water, and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous MgSO4(s), and concentrated under reduced pressure to give N-(4-(2-bromoacetyl)-3,5-dimethylphenyl)acetamide (7.00 g), which was used directly for the next step without further purification.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. additionadded with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous MgSO4(s)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-21b9b5e8755944ceb606fd1f1db31ecc
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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