Acetic Anhydride → N-(5-bromo-2-fluorophenyl)acetamide

HRID 1059176Notes

Reaction equation

HRID 1059176 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([N+:9]([O-])=O)[CH:3]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13]>C(O)(=O)C.[Fe]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([NH:9][C:12](=[O:14])[CH3:13])[CH:3]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 242827N-(5-bromo-2-fluorophenyl)acetamide

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

4-Bromo-1-fluoro-2-nitrobenzene (5.81 g), iron powder (6.20 g) and acetic anhydride (5 ml) were stirred in acetic acid (50 ml) at 60° C. for 16 h. Acetic acid was evaporated under reduced pressure and water and ethyl acetate were added. The organic layer was washed with aqueous sodium hydrogen carbonate and brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from hexane-ethyl acetate to give the title compound (3.56 g) as colorless prism crystals.

Workup

  1. customAcetic acid was evaporated under reduced pressure and water and ethyl acetate
  2. additionwere added
  3. washThe organic layer was washed with aqueous sodium hydrogen carbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-479750fc38424d3189c3949793422546
Source dataset
uspto-grants-2003_02
Patent number
US06518257B1

Reaction notes

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