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

HRID 1010630Notes

Reaction equation

HRID 1010630 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.OS(O)(=O)=O.N([O-])=O.[Na+]>C(O)C>[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

5

Reactant 3

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

Product 1

HCID 2387111,3-dibromo-5-nitrobenzeneYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To an ice-cold solution of 2,6-dibromo-4-nitro-aniline (100 g, 0.34 mol) in 1.50 L of ethanol was added dropwise conc. H2SO4 (116 ml, 2.15 mol) over 30-45 min with constant stirring. The reaction mixture was heated to 60° C. and sodium nitrite (72 g, 1.09 mol) was added to the reaction mixture portion wise. The resulting yellow colored reaction mixture was heated slowly to 90° C. and refluxed for 2 to 2.5 h. After cooling to room temperature, the mixture was poured into ice water. The reddish brown solid thus obtained was filtered, washed with water and dried to give the desired compound as a brown solid (85.0 g, 90%).

Workup

  1. temperatureThe resulting yellow colored reaction mixture was heated slowly to 90° C.
  2. temperaturerefluxed for 2 to 2.5 h
  3. temperatureAfter cooling to room temperature
  4. customThe reddish brown solid thus obtained
  5. filtrationwas filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-61ffae1378eb40fdbc99237932728925
Source dataset
uspto-grants-2011_07
Patent number
US07977340B2

Reaction notes

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