Water → 2-Bromo-4-(tert-butyl)-6-nitroaniline

HRID 1930261Notes

Reaction equation

HRID 1930261 reaction equation
[C:1]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[BrH:15].[NH+]1C=CC=CC=1.O.S([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C>[Br:15][C:10]1[CH:11]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=[C:7]([N+:12]([O-:14])=[O:13])[C:8]=1[NH2:9]

Participants

6

Reactant 4

HCID 962WaterHCID 24437Sodium SulfiteHCID 805734-tert-Butyl-2-nitroanilineHCID 21226041Pyridinium hydrobromide

Product 1

HCID 509978562-Bromo-4-(tert-butyl)-6-nitroanilineYield 94%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of 4-tert-butyl-2-nitroaniline (1.033 g, 5.32 mmol) in glacial acetic acid (7.8 mL) was warmed with a heat gun until all solids had dissolved. The solution was then cooled and treated portion wise with pyridinium hydrobromide perbromide (1.96 g, 6.12 mmol). After addition, the solution was stirred at room temperature for 1 h. The mixture was added to water (50 mL) and treated with a small amount of sodium sulfite. After stirring for 30 min, the precipitate was collected by filtration. The solid obtained was washed with water and dissolved in EtOAc. Washed with water and brine. Dried over Na2SO4, filtered and concentrated under vacuum to provide the title compound as a yellow-orange solid (1.36 g, 94%).

Workup

  1. temperaturewas warmed with a heat gun until all solids
  2. dissolutionhad dissolved
  3. temperatureThe solution was then cooled
  4. additionAfter addition
  5. stirringAfter stirring for 30 min
  6. filtrationthe precipitate was collected by filtration
  7. customThe solid obtained
  8. washwas washed with water
  9. dissolutiondissolved in EtOAc
  10. washWashed with water and brine
  11. dry with materialDried over Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0058c22e5b9846b5b231628355afefde
Source dataset
uspto-grants-2012_05
Patent number
US08188104B2

Reaction notes

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