N-bromobutanimide → 4-bromo-2-tert-butylphenylamine

HRID 1844693Notes

Reaction equation

HRID 1844693 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].C1C(=O)N([Br:19])C(=O)C1>CN(C=O)C.O>[Br:19][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 2

HCID 67184N-bromobutanimideHCID 805742-tert-Butylaniline

Product 1

HCID 119590004-bromo-2-tert-butylphenylamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-tert-butylaniline (14.9 g, 100 mmol) was added a solution of NBS (17.8 g, 100 mmol) in DMF at rt. The reaction mixture was stirred for 1 h at rt, diluted with water (30 mL) and extracted with Et2O (3×250 mL). The organic layer was washed with brine, dried over Na2SO4, concentrated and purified by CC to give compound P25a (19 g, 83%).

Workup

  1. extractionextracted with Et2O (3×250 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by CC
  6. customto give compound P25a (19 g, 83%)

Sources & evidence

ORD record
ord-1dd70b49691f4e828da0d36df0947067
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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