Sulfuric Acid → 1-Bromo-2,5-dichloro-3-nitrobenzene

HRID 429139

Reaction equation

HRID 429139 reaction equation
S(=O)(=O)(O)O.[Br:6][C:7]1[C:13]([Cl:14])=[C:12]([N+:15]([O-:17])=[O:16])[C:11](Cl)=[CH:10][C:8]=1N.N([O-])=O.[Na+].[Cl:23]CCl>C(O)C.C(=O)([O-])O.[Na+]>[Br:6][C:7]1[C:13]([Cl:14])=[C:12]([N+:15]([O-:17])=[O:16])[CH:11]=[C:10]([Cl:23])[CH:8]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 183545642-Bromo-3,5-dichloro-4-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 183545541-Bromo-2,5-dichloro-3-nitrobenzeneYield 80%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Concentrated sulphuric acid (2.2 ml) was slowly added to a suspension of 2-bromo-3,5-dichloro-4-nitroaniline (D8) (0.9 g, 3.1 mmol) in ethanol (20 ml). The resulting solution was heated to reflux and crushed sodium nitrite (478 mg, 6.9 mmol) was added in two portions. After 0.5 h at reflux, the mixture was cooled, diluted with dichloromethane (50 ml) and saturated sodium hydrogen carbonate solution (50 ml) was added. The layers were separated and the organic phase dried (Na2SO4) and concentrated to an oil which was purified by column chromatography over silica gel eluting with a gradient of ethyl acetate/hexane to give the title compound (D9) as an orange solid (0.67 g, 80%), MH+ 269/271.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux
  3. additionwas added in two portions
  4. temperatureAfter 0.5 h at reflux
  5. temperaturethe mixture was cooled
  6. additionwas added
  7. customThe layers were separated
  8. dry with materialthe organic phase dried (Na2SO4)
  9. concentrationconcentrated to an oil which
  10. customwas purified by column chromatography over silica gel eluting with a gradient of ethyl acetate/hexane

Sources & evidence

ORD record
ord-f3d99b8097e947bf84a8f0afd32323f5
Source dataset
uspto-grants-2001_11
Patent number
US06316450B1

Linked notes

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