Nitric Acid → N-(4-bromo-2-nitrophenyl)acetamide

HRID 2093044Notes

Reaction equation

HRID 2093044 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[N+:12]([O-])([OH:14])=[O:13].OS(O)(=O)=O>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:6]([N+:12]([O-:14])=[O:13])[CH:7]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 76834'-Bromoacetanilide

Product 1

HCID 136690N-(4-bromo-2-nitrophenyl)acetamideYield 95%

Procedure

N-(4-Bromophenyl)acetamide obtained in step I above was nitrated using nitric acid (1.2 eq)+H2SO4 (1.0 eq) at 0 to 5° C. for 2 hrs. After the completion of the reaction, reaction mixture was added to ice and pH was adjusted to 8, extracted with dichloromethane, which was evaporated to dryness to obtain N-(4-bromo-2-nitrophenyl)acetamide. (Yield=95%)

Workup

  1. customat 0 to 5° C.
  2. customfor 2 hrs
  3. customAfter the completion of the reaction, reaction mixture
  4. additionwas added to ice and pH
  5. extractionextracted with dichloromethane, which
  6. customwas evaporated to dryness

Sources & evidence

ORD record
ord-1660a4d72c624b3fb70ce9e325c62255
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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