Water → 4-bromo-2-tert-butylphenylamine

HRID 534821Notes

Reaction equation

HRID 534821 reaction equation
[C:1]([C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[NH2:7])([CH3:4])([CH3:3])[CH3:2].[Br-:12].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[Br:12][C:10]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 805742-tert-ButylanilineHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 119590004-bromo-2-tert-butylphenylamineYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-tert-butylaniline (50 g, 335 mmol) in THF (500 mL) was added tetrabutylammonium tribromide (234.5 g, 335 mmol) at 0° C. After the solution was stirred for 30 minutes at that temperature, it was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated Na2S2O3 solution and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the crude product. The product was purified by flash column chromatography (silica gel, n-hexane/ethyl acetate=100:0 to 20:80) to provide 4-bromo-2-tert-butylaniline (74.6 g, 98%) as a pink oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated Na2S2O3 solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give the crude product
  6. customThe product was purified by flash column chromatography (silica gel, n-hexane/ethyl acetate=100:0 to 20:80)

Sources & evidence

ORD record
ord-579d8ff537f9416b9e7a45def59d3e5e
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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