Acetic Anhydride → N-(2-Fluorophenyl)acetamide

HRID 72823

Reaction equation

HRID 72823 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[F:8][C:9]1[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=1[NH2:11]>O>[C:5]([NH:11][C:10]1[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=1[F:8])(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 95842-Fluoroaniline

Product 1

HCID 67860N-(2-Fluorophenyl)acetamideYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
65 °C

Procedure

Acetic anhydride (57 mL, 0.6 mol) was added slowly, over approximately 40 min., to stirred 2-fluoroaniline (55.7 g, 0.5 mol) under cooling (water bath) to maintain the reaction temperature at 60-70° C. After 10 more hours the reaction mixture was poured into H2O, the whole was extracted with ethyl acetate (2×300 mL). The combined organic extracts were washed with 5% aqueous NaHCO3, brine, dried (K2CO3), filtered and concentrated to provide the title compound as a white solid (67.0 g, 88%).

Workup

  1. extractionthe whole was extracted with ethyl acetate (2×300 mL)
  2. washThe combined organic extracts were washed with 5% aqueous NaHCO3, brine
  3. dry with materialdried (K2CO3)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-614b9d3a1d774b029c33f5ca7a6e934e
Source dataset
uspto-grants-2014_09
Patent number
US08828986B2

Linked notes

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