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

HRID 1784801Notes

Reaction equation

HRID 1784801 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 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(The named compound was synthesized according to Dumont, Bull. Soc. Chim. Bel., 505 (1995). This compound is also commercially available from Karl Industries, Aurora, Ohio.) To a suspension of 2,6-dibromo-4-nitroaniline (75.0 g, 254 mmol) in ethanol (1 L) was added H2SO4 (100 mL). The mixture was heated to reflux and sodium nitrite (50.5 g, 730 mmol) was added portion-wise over a period of 15 min. The mixture was heated at reflux for 3 h and was then cooled to room temperature. The formed thick suspension was poured on ice water (1000 mL) upon which more solid precipitated. The solid was filtered and the filter cake washed with water (2×250 mL) and dried in an oven at 20 mbar/30° C. to give 66.2 g (93%) of 1,3-dibromo-5-nitrobenzene as a brown solid.

Workup

  1. custom(The named compound was synthesized
  2. temperatureThe mixture was heated
  3. temperatureto reflux
  4. temperatureThe mixture was heated
  5. temperatureat reflux for 3 h
  6. additionThe formed thick suspension was poured on ice water (1000 mL) upon which more solid
  7. customprecipitated
  8. filtrationThe solid was filtered
  9. washthe filter cake washed with water (2×250 mL)
  10. customdried in an oven at 20 mbar/30° C.

Sources & evidence

ORD record
ord-f9ddc22aff564f9bb539977507e82d66
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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