Acetic Anhydride → N-(4-Bromo-2-methylphenyl)acetamide

HRID 2216249

Reaction equation

HRID 2216249 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[Br:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[C:11]([CH3:16])[CH:10]=1.C([O-])(=O)C.[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:16][C:11]1[CH:10]=[C:9]([Br:8])[CH:15]=[CH:14][C:12]=1[NH:13][C:5]([CH3:6])=[O:7]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 114234-Bromo-2-methylanilineHCID 517045Sodium Acetate

Product 1

HCID 222277N-(4-Bromo-2-methylphenyl)acetamideYield 99.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

Acetic anhydride (15.2 ml, 0.16 mol) was added dropwise to a stirred mixture of 4-bromo-2-methylaniline (10.0 g, 0.054 mol) and sodium acetate (2.52 g, 0.056 mol) in toluene (150 ml). Once the addition was complete the mixture was warmed to 85° C. and stirred for 40 minutes. The mixture was cooled to room temperature, diluted with ethyl acetate and washed with water. The organic solution was evaporated in vacuo, a further quantity of toluene was added and then the solvent was evaporated to give 4-bromo-2-methylacetanilide (12.3 g), as a colourless solid.

Workup

  1. additionOnce the addition
  2. temperatureThe mixture was cooled to room temperature
  3. washwashed with water
  4. customThe organic solution was evaporated in vacuo
  5. additiona further quantity of toluene was added
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-469f6efd7aa8437e88791e175f260172
Source dataset
uspto-grants-2006_09
Patent number
US07112553B1

Linked notes

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