4-Bromoaniline → 4'-Bromoacetanilide

HRID 1004775Notes

Reaction equation

HRID 1004775 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]>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

4

Reactant 2

HCID 78074-BromoanilineHCID 7918Acetic Anhydride

Product 1

HCID 76834'-BromoacetanilideYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

In an atmosphere of argon, 50 g (290.7 mmols) of 4-bromoaniline was dissolved in 580 ml of methanol, and the solution obtained was cooled to 0° C., and thereafter 32.6g (1.1-fold equivalent weight) of acetic anhydride was dropwise added thereto. Thereafter, the solution obtained was restored to room temperature, followed by stirring for 1 hour, and the crystals deposited were filtered off. To the residue obtained by vacuum concentration of the filtrate, 250 ml of water was added, and the crystals deposited were collected by filtration, which was then washed with water, followed by natural drying to obtain 65.5 g of N-acetyl-4-bromoaniline (yield: 100%; a white solid).

Workup

  1. customthe solution obtained
  2. customThereafter, the solution obtained
  3. customwas restored to room temperature
  4. filtrationthe crystals deposited were filtered off
  5. customTo the residue obtained by vacuum concentration of the filtrate, 250 ml of water
  6. additionwas added
  7. filtrationthe crystals deposited were collected by filtration, which
  8. washwas then washed with water
  9. customby natural drying

Sources & evidence

ORD record
ord-4ad17b3f53014e838ef5a354e3ff8f25
Source dataset
uspto-grants-2000_04
Patent number
US06051722

Reaction notes

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