Acetic Anhydride → n-(2,5-difluorophenyl)acetamide

HRID 1078003Notes

Reaction equation

HRID 1078003 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:3]=1[NH2:4].[C:10](OC(=O)C)(=[O:12])[CH3:11]>S(=O)(=O)(O)O>[F:1][C:2]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:3]=1[NH:4][C:10](=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 677752,5-Difluoroaniline

Product 1

HCID 242830n-(2,5-difluorophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

2,5-Difluoroaniline (100 g, 0.775 mol) is added dropwise to a mixture of concentrated sulfuric acid (4 drops) in acetic anhydride (250 mL) while maintaining the reaction mixture temperature below 15° C. After the addition is complete, the reaction mixture is stirred for one hour and filtered to obtain a solid. The solid is washed with diethyl ether and air dried to give the title product as a white solid, mp 124°-125° C.

Workup

  1. temperaturewhile maintaining the reaction mixture temperature below 15° C
  2. additionAfter the addition
  3. filtrationfiltered
  4. customto obtain a solid
  5. washThe solid is washed with diethyl ether and air
  6. customdried

Sources & evidence

ORD record
ord-73aa77dbb1e34867bdd28fb3b3f9bb67
Source dataset
uspto-grants-1996_08
Patent number
US05545742

Reaction notes

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