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

HRID 912866Notes

Reaction equation

HRID 912866 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). The combined organic extracts were washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (25% EtOAc/hexane) to give the title compound as a yellow solid. MS (ESI, neg. ion) m/z: 325.0 (M−1).

Workup

  1. stirringThe resulting solution was stirred at room temperature for 3 h
  2. additionpoured
  3. extractionextracted with EtOAc (3×200 mL)
  4. washThe combined organic extracts were washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (25% EtOAc/hexane)

Sources & evidence

ORD record
ord-2c73324a3bdf4379ae862b8be9823dce
Source dataset
uspto-grants-2011_09
Patent number
US08026241B2

Reaction notes

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