Hydrogen Bromide → Benzene, 1,2,3-tribromo-5-nitro-

HRID 1091015Notes

Reaction equation

HRID 1091015 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[C:5]([Br:12])[C:3]=1N.N([O-])=O.[Na+].[BrH:17]>C(O)(=O)C.S(=O)(=O)(O)O.O.[Cu]Br>[Br:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[C:5]([Br:12])[C:3]=1[Br:17]

Participants

8

Reactant 3

HCID 260Hydrogen BromideHCID 132312,6-Dibromo-4-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 640602Benzene, 1,2,3-tribromo-5-nitro-

Reagents, catalysts & solvents 4

HCID 24593copper(I) bromideCatalystHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
20 °C

Procedure

At 20° C., with stirring and cooling with ice, a solution of 2,6-dibromo-4-nitro-aniline (47.2 g) in acetic acid (1.6 liters) is slowly poured into a solution of sodium nitrite (12 g) in concentrated sulphuric acid (85 ml). Then, the mixture is stirred for 20 minutes at ambient temperature. The solution thus prepared is then slowly added with stirring and cooling with ice to a solution of copper (I) bromide (12.8 g) in 63% hydrobromic acid (40 ml). After it has all been added the mixture is stirred for a further 30 minutes. It is diluted with water, the precipitate is filtered off and washed with water. This crude product is recrystallized from methanol.

Workup

  1. temperaturecooling with ice
  2. stirringThen, the mixture is stirred for 20 minutes at ambient temperature
  3. customThe solution thus prepared
  4. additionis then slowly added
  5. stirringwith stirring
  6. additionall been added the mixture
  7. stirringis stirred for a further 30 minutes
  8. filtrationthe precipitate is filtered off
  9. washwashed with water
  10. customThis crude product is recrystallized from methanol

Sources & evidence

ORD record
ord-97d9ac1422b940268226f2fbe421678e
Source dataset
uspto-grants-1992_01
Patent number
US05084449

Reaction notes

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