Acetic Anhydride → N-[3-bromo-5-(trifluoromethyl)phenyl]acetamide

HRID 2198048Notes

Reaction equation

HRID 2198048 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1)[NH2:5].[C:13](OC(=O)C)(=[O:15])[CH3:14]>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:13](=[O:15])[CH3:14])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 27358803-Bromo-5-(trifluoromethyl)aniline

Product 1

HCID 21959349N-[3-bromo-5-(trifluoromethyl)phenyl]acetamideYield 109.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-bromo-5-(trifluoromethyl)aniline (10 g) in pyridine (50 mL) was added acetic anhydride (5.6 g) at 0° C., and the mixture was stirred at room temperature for 16 hr. The reaction mixture was concentrated, 1M hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with 1M hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution, and saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated to give the title compound (12.9 g, yield quant.) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition1M hydrochloric acid was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with 1M hydrochloric acid, saturated aqueous sodium hydrogencarbonate solution, and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-0d8eef0cb955412b94f0e7beb2f8d44b
Source dataset
uspto-grants-2012_12
Patent number
US08338622B2

Reaction notes

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