Water → 4'-Bromoacetanilide

HRID 356222Notes

Reaction equation

HRID 356222 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9](OC(=O)C)(=[O:11])[CH3:10].O>CO>[C:9]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([Br:1])=[CH:3][CH:4]=1)(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 78074-BromoanilineHCID 7918Acetic Anhydride

Product 1

HCID 76834'-BromoacetanilideYield 99.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

In an atmosphere of argon, 25 g (145.3 mmols) of 4-bromoaniline was dissolved in 50 ml of methanol, and the solution obtained was cooled to 0° C., and thereafter 27.4 ml (2.0-fold equivalent weight) of acetic anhydride was dropwise added thereto. Thereafter, the solution obtained was restored to room temperature, and stirred for 20 minutes. To the reaction solution obtained, 250 ml of water was added, and a white solid deposited was collected by filtration, which was then washed with water, followed by natural drying to obtain 30.8 g of N-acetyl-4-bromoaniline (yield: 99.1%; a while solid).

Workup

  1. customthe solution obtained
  2. customThereafter, the solution obtained
  3. customwas restored to room temperature
  4. customTo the reaction solution obtained
  5. filtrationa white solid deposited was collected by filtration, which
  6. washwas then washed with water
  7. customby natural drying

Sources & evidence

ORD record
ord-f08664d5a6a9470fa3143a923571601a
Source dataset
uspto-grants-1998_11
Patent number
US05834575

Reaction notes

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