Acetic Anhydride → N-(3-Bromophenyl)acetamide

HRID 912249Notes

Reaction equation

HRID 912249 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[C:9](OC(=O)C)(=[O:11])[CH3:10]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:9](=[O:11])[CH3:10])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 115623-Bromoaniline

Product 1

HCID 12123N-(3-Bromophenyl)acetamideYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane solution (15 ml) of 3-bromoaniline (1 g), acetic anhydride (659 μl) was added, followed by stirring at room temperature for 14 hours. This was washed with water (20 ml), and the organic layer was dried over sodium sulfate. After filtering off the sodium sulfate, the solvent was distilled off under reduced pressure. This was purified by silica gel column chromatography (dichloromethane/methanol=200/1), to obtain the desired compound (1.19 g, 96%).

Workup

  1. washThis was washed with water (20 ml)
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. filtrationAfter filtering off the sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThis was purified by silica gel column chromatography (dichloromethane/methanol=200/1)

Sources & evidence

ORD record
ord-f1015a6ec1d24e488681d992bc221da4
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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