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

HRID 130407Notes

Reaction equation

HRID 130407 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([CH:8]=1)[NH2:7].[C:10](OC(=O)C)(=[O:12])[CH3:11]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:9])=[C:6]([NH:7][C:10](=[O:12])[CH3:11])[CH:8]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 27694075-Bromo-2-fluoroaniline

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Bromo-2-fluoroaniline (14.79 g, 78 mmol) was heated at reflux in acetic acid (50 ml) and acetic anhydride (50 ml) for 8 hours. The solution was concentrated in vacuo, azeotroping with toluene. The residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic phase was washed with water (×3), brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by chromatography on silica gel (gradient of hexane to ethyl acetate) to afford the title compound. MS (ES+) m/e 232/234 [M+H]+.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customazeotroping with toluene
  3. customThe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  4. washThe organic phase was washed with water (×3), brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography on silica gel (gradient of hexane to ethyl acetate)

Sources & evidence

ORD record
ord-f55096a018ad42e2b086d20d4c9e6e86
Source dataset
uspto-grants-2008_06
Patent number
US07381728B2

Reaction notes

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