Potassium Nitrate → 2-Bromo-4-tert-butyl-5-nitroaniline

HRID 1404067Notes

Reaction equation

HRID 1404067 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[NH2:12].[N+:13]([O-])([O-:15])=[O:14].[K+]>OS(O)(=O)=O>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:9])([CH3:11])[CH3:10])[C:5]([N+:13]([O-:15])=[O:14])=[CH:4][C:3]=1[NH2:12]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 2385912-Bromo-4-(tert-butyl)aniline

Product 1

HCID 574826962-Bromo-4-tert-butyl-5-nitroanilineYield 78%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
-7.5 °C

Procedure

2-Bromo-4-tert-butyl-phenylamine (160 g, 0.71 mol) was added dropwise to H2SO4 (410 mL) at room temperature to yield a clear solution. This clear solution was then cooled down to −5 to −10° C. A solution of KNO3 (83 g, 0.82 mol) in H2SO4 (410 mL) was added dropwise while the temperature was maintained between −5 to −10° C. Upon completion, the reaction mixture was poured into ice/water and extracted with EtOAc. The combined organic layers were washed with 5% Na2CO3 and brine, dried over Na2SO4 and concentrated. The residue was purified by a column chromatography (ethyl acetate/petroleum ether 1:10) to give 2-bromo-4-tert-butyl-5-nitro-phenylamine as a yellow solid (150 g, 78%).

Workup

  1. customto yield a clear solution
  2. temperaturewas maintained between −5 to −10° C
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with 5% Na2CO3 and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by a column chromatography (ethyl acetate/petroleum ether 1:10)

Sources & evidence

ORD record
ord-fc5d631e5a3541df9ec6dead470ff3b3
Source dataset
uspto-grants-2014_12
Patent number
US08912199B2

Reaction notes

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