Sulfuric Acid → 1,3-dibromo-5-nitrobenzene

HRID 972668Notes

Reaction equation

HRID 972668 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.C(O)(C)C.S(=O)(=O)(O)O.N([O-])=O.[Na+]>O>[Br:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[C:5]([Br:12])[CH:3]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 132312,6-Dibromo-4-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 2387111,3-dibromo-5-nitrobenzeneYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

296 parts of 2,6-dibromo-4-nitro-aniline are introduced into 400 parts of isopropanol and 750 parts of water and 130 parts of concentrated sulfuric acid (98 percent strength by weight) are then added to the mixture. A solution of 105 parts of NaNO2 in 150 parts of water is run in at 70° C. as described in Example 1. The mixture is cooled, 300 parts of water are added and the product is filtered off. 278 parts of 3,5-dibromo-nitro-benzene (99% of theory), of melting point 102°-104° C., are obtained.

Workup

  1. additionare then added to the mixture
  2. customis run in at 70° C.
  3. temperatureThe mixture is cooled
  4. filtrationthe product is filtered off

Sources & evidence

ORD record
ord-0b82c481134d4f60ab1fedac893bed63
Source dataset
uspto-grants-1977_10
Patent number
US04053527

Reaction notes

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