Acetic Anhydride → N-(3-fluoro-2-methylphenyl)acetamide

HRID 1988962Notes

Reaction equation

HRID 1988962 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH3:9].[C:10](OC(=O)C)(=[O:12])[CH3:11]>>[F:8][C:4]1[C:3]([CH3:9])=[C:2]([NH:1][C:10](=[O:12])[CH3:11])[CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 2855533-Fluoro-2-methylaniline

Product 1

HCID 1489284N-(3-fluoro-2-methylphenyl)acetamide

Procedure

1-amino-3-fluoro-2-methylbenzene (1 equivalent) was dissolved in CH2C2 and acetic anhydride (2.0 equivalents) was added slowly. The solution was stirred at room temperature for 4 hours. The reaction mixture was then quenched with water, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with H2O, a 10% HCl solution, H2O, and brine. It was then dried over Na2SO4 and concentrated in vacuo, to yield N-(3-fluoro-2-methylphenyl)acetamide as a pink solid. LC/MS (m/z) 168.2 (MH+), Rt 1.91 minutes.

Workup

  1. additionwas added slowly
  2. customThe reaction mixture was then quenched with water
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe organic layer was washed with H2O
  5. dry with materialIt was then dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c7a52fa0b71e44c287951a6502186035
Source dataset
uspto-grants-2010_01
Patent number
US07642278B2

Reaction notes

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