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

HRID 2041917Notes

Reaction equation

HRID 2041917 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]>C(O)(=O)C>[CH3:5][C:6]1[C:11]([N+:1]([O-:4])=[O:2])=[CH:10][CH:9]=[C:8]([CH3:12])[C:7]=1[Br:13]

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

Conditions

Temperature
80 °C

Procedure

Fuming nitric acid (83.3 mL) (>90%) was added slowly to a solution of 2,6-dimethyl bromobenzene (27.9 g, 150 mmol) in acetic acid (167 mL) and cooled in an ice-bath (above f.p). The mix was allowed to come to rt and later heated at 80° C. for 2 h. (HPLC showed no SM). Reaction mixture was cooled and poured into ice-water with stirring. The resulting yellow solid was filtered, washed with ice-water and dried to give 28.7 g of an yellow solid which was used as such in the next step.

Workup

  1. temperaturecooled in an ice-bath (above f.p)
  2. customto come to rt
  3. customReaction mixture
  4. temperaturewas cooled
  5. filtrationThe resulting yellow solid was filtered
  6. washwashed with ice-water
  7. customdried

Sources & evidence

ORD record
ord-3aa6b4bc4dc5441a9236c23f83211ace
Source dataset
uspto-grants-2013_11
Patent number
US08586566B2

Reaction notes

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