Nitric Acid → 1-Bromo-2,5-dimethyl-4-nitrobenzene

HRID 988933Notes

Reaction equation

HRID 988933 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[CH3:9].[N+:10]([O-])([OH:12])=[O:11].S(=O)(=O)(O)O>C(OC(=O)C)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=1[CH3:9]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 11121Benzene, 2-bromo-1,4-dimethyl-

Product 1

HCID 8258081-Bromo-2,5-dimethyl-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

740 g of bromo-p-xylene were initially introduced in acetic anhydride (ice-bath cooling) and nitrating acid (prepared from 400 ml of fuming nitric acid and 480 ml of concentrated sulfuric acid) was slowly added dropwise. During the addition, it was ensured that the internal temperature remained between 22° C.-25° C. When the addition was complete (duration about 5 hours), the ice bath was removed, and the mixture was stirred at RT for about a further 1 hour.

Workup

  1. additionwas slowly added dropwise
  2. additionDuring the addition, it
  3. customremained between 22° C.-25° C
  4. additionWhen the addition
  5. customthe ice bath was removed

Sources & evidence

ORD record
ord-8b59aa4053fd431bafb677517bdcba32
Source dataset
uspto-grants-2003_10
Patent number
US06638646B2

Reaction notes

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