2,6-Dibromo-4-nitroaniline → 1,3-dibromo-5-nitrobenzene

HRID 1190892Notes

Reaction equation

HRID 1190892 reaction equation
N([O-])=O.[Na+].[Br:5][C:6]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[C:9]([Br:16])[C:7]=1N>OS(O)(=O)=O.CCOC(C)=O>[Br:5][C:6]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[C:9]([Br:16])[CH:7]=1

Participants

5

Reactant 2

HCID 132312,6-Dibromo-4-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 2387111,3-dibromo-5-nitrobenzeneYield 41%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

NaNO2 (4.1 g, 59.1 mmol) was added portionwise to a solution of 2,6-dibromo-4-nitroaniline (5 g, 3.5 eq) in 20% H2SO4 and AcOEt (each 40 mL) at a rate to keep the internal temperature at 50-55° C. After heating for an additional 10 min, the mixture was cooled, diluted, and extracted with AcOEt. The combined organic layers were dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography (cyclohexane/DCM//7/3 then 8/2) to yield expected compound as a white solid (1.94 g, 41% yield).

Workup

  1. customat 50-55° C
  2. temperatureAfter heating for an additional 10 min
  3. temperaturethe mixture was cooled
  4. additiondiluted
  5. extractionextracted with AcOEt
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash chromatography (cyclohexane/DCM//7/3

Sources & evidence

ORD record
ord-16c9d95e86ca435ba261a1e582db22e1
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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