Hydrogen Peroxide → N-(2-Bromo-4,5-dimethylphenyl)acetamide

HRID 963607Notes

Reaction equation

HRID 963607 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].[C:10]([O:13]C(=O)C)(=O)[CH3:11].[Br:17]Br.OO>C(O)(=O)C.O>[CH3:1][C:2]1[C:8]([CH3:9])=[CH:7][C:6]([Br:17])=[C:4]([NH:5][C:10]([CH3:11])=[O:13])[CH:3]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 72483,4-DimethylanilineHCID 7918Acetic AnhydrideHCID 24408Bromine

Product 1

HCID 890424N-(2-Bromo-4,5-dimethylphenyl)acetamideYield 182.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 50.0 g (0.41 mol) of 3,4-dimethylaniline in 250 mL of glacial acetic acid was added 46.0 g (0.45 mol) of acetic anhydride was added dropwise with ice-bath cooling. The reaction was heated for 15 minutes at 120° C., then cooled to 10° C. Bromine (32.8 g, 0.21 mol) was added dropwise over 25 minutes. The addition funnel was washed with a small amount of acetic acid, and 27.2 g (0.24 mol) of 30% hydrogen peroxide was added over 30 minutes. The reaction was stirred for 2 hours at 10°-15° C. and then poured into 1200 mL of cold water. The precipitated product was collected by filtration, washed with water, and dried under vacuum to give 93.0 g (94% yield) of crude 2-bromo-4,5-dimethylacetanilide which was used without further purification.

Workup

  1. additionwas added dropwise with ice-bath
  2. temperaturecooling
  3. temperaturecooled to 10° C
  4. additionwas added over 30 minutes
  5. filtrationThe precipitated product was collected by filtration
  6. washwashed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-bf9033ffe2c14f0ea9f2225a940d518a
Source dataset
uspto-grants-1998_06
Patent number
US05763608

Reaction notes

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