Nitric Acid → N-[4-Bromo-2-nitro-5-(trifluoromethyl)phenyl]acetamide

HRID 730806Notes

Reaction equation

HRID 730806 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13].[N+:16]([O-])([OH:18])=[O:17].C([O-])(O)=O.[Na+]>S(=O)(=O)(O)O>[Br:1][C:2]1[C:3]([C:12]([F:13])([F:14])[F:15])=[CH:4][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:6]([N+:16]([O-:18])=[O:17])[CH:7]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 697838N-[4-Bromo-3-(trifluoromethyl)phenyl]acetamide

Product 1

HCID 11709640N-[4-Bromo-2-nitro-5-(trifluoromethyl)phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the acetamide from step (a) above (8.46 g, 30 mmol) in concentrated sulfuric acid (32.5 mL) was added dropwise concentrated HNO3 (4.1 mL, 90%. J. T. Baker) with stirring at 0° C. The resulting solution was stirred at room temperature for 3 h and poured into crushed ice (80 mL). The mixture was carefully neutralized with solid NaHCO3 and extracted with EtOAc (3×200 mL).

Workup

  1. stirringThe resulting solution was stirred at room temperature for 3 h
  2. additionpoured
  3. extractionextracted with EtOAc (3×200 mL)

Sources & evidence

ORD record
ord-fa2ff64d38474f399849acfd0226a069
Source dataset
uspto-grants-2009_09
Patent number
US07582761B2

Reaction notes

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