Nitric Acid → 1,3-Dibromo-2-methyl-4-nitrobenzene

HRID 653535Notes

Reaction equation

HRID 653535 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[CH3:9].[N+:10]([O-])([OH:12])=[O:11]>>[Br:1][C:2]1[C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=[C:4]([Br:8])[C:3]=1[CH3:9]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 346812,6-Dibromotoluene

Product 1

HCID 138854011,3-Dibromo-2-methyl-4-nitrobenzene

Procedure

To 38 g of 2,6-dibromotoluene (0.152 mol) was added dropwise with stirring, over a period of thirty minutes, 76 ml of 70% nitric acid. An exothermic reaction was observed. The resulting mixture was stirred for an additional sixty minutes, after which time the mixture was poured into 1500 ml of ice water. The solids which separated were collected by filtration and dried to yield 44.62 g of 2,6-dibromo-3-nitrotoluene. Recrystallization of the reaction product from ethyl alcohol-water yielded material melting at 47°-48° C.

Workup

  1. customAn exothermic reaction
  2. stirringThe resulting mixture was stirred for an additional sixty minutes
  3. customThe solids which separated
  4. filtrationwere collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-c48db44cf5be4e2385d65796faed23fd
Source dataset
uspto-grants-1987_06
Patent number
US04677219

Reaction notes

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