Nitric Acid → 2-Bromo-1,3-dimethyl-4-nitrobenzene

HRID 2278388Notes

Reaction equation

HRID 2278388 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:7]=1[Br:13]>CC(O)=O>[Br:13][C:7]1[C:6]([CH3:5])=[C:11]([N+:1]([O-:4])=[O:2])[CH:10]=[CH:9][C:8]=1[CH3:12]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 684712-Bromo-m-xylene

Product 1

HCID 123959052-Bromo-1,3-dimethyl-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Fuming nitric acid (32.5 ml) was slowly added to a solution of 2,6-dimethyl-bromobenzene (10 g, 54 mmol) in AcOH (75 ml) cooled in an ice bath. The resulting mixture was allowed to warm to room temperature, stirred for 1 h, and heated at 80° C. for 2 h. The reaction mixture was cooled to room temperature and poured into ice water with stirring. The resultant precipitate was collected by suction filtration to afford the title compound (10 g) which was used without further purification.

Workup

  1. temperaturecooled in an ice bath
  2. temperatureheated at 80° C. for 2 h
  3. temperatureThe reaction mixture was cooled to room temperature
  4. stirringwith stirring
  5. filtrationThe resultant precipitate was collected by suction filtration

Sources & evidence

ORD record
ord-57330c7851a24d31843c17382316b668
Source dataset
uspto-grants-2015_09
Patent number
US09133180B2

Reaction notes

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