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

HRID 2197400Notes

Reaction equation

HRID 2197400 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13]>C(O)(=O)C>[CH3:13][C:7]1[C:8]([N+:1]([O-:4])=[O:2])=[CH:9][CH:10]=[C:11]([CH3:12])[C:6]=1[Br:5]

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 (>90% yellow fuming HNO3) is slowly added to a solution of 2-bromo-m-xylene (20 g, 150 mmol) in acetic acid (100 mL) cooled in an ice bath (above freezing point). The resulting mixture is allowed to warm to room temperature, stirred for 1 h, and heated at 80° C. for 2 h or until the reaction is complete by GC/MS analysis following micro-scale base work-up. The reaction mixture is cooled to room temperature and poured into ice/water with stirring. The resulting yellow precipitates are collected by suction filtration and air dried to obtain 2,6-dimethyl-3-nitrobromobenzene.

Workup

  1. temperaturecooled in an ice bath (above freezing point)
  2. temperatureheated at 80° C. for 2 h or until the reaction
  3. temperatureThe reaction mixture is cooled to room temperature
  4. stirringwith stirring
  5. customThe resulting yellow precipitates
  6. filtrationare collected by suction filtration and air
  7. customdried

Sources & evidence

ORD record
ord-b53100ce65c24490a2d485a167ce6d04
Source dataset
uspto-grants-2012_12
Patent number
US08338591B2

Reaction notes

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