N-bromobutanimide → 2-Bromo-4-(tert-butyl)aniline

HRID 401284Notes

Reaction equation

HRID 401284 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:19])C(=O)C1>CN(C=O)C.O>[Br:19][C:9]1[CH:10]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=[CH:7][C:8]=1[NH2:11]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 698614-Tert-Butylaniline

Product 1

HCID 2385912-Bromo-4-(tert-butyl)aniline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4-tert-butyl-phenylamine (447 g, 3 mol) in DMF (500 mL) was added dropwise NBS (531 g, 3 mol) in DMF (500 mL) at room temperature. Upon completion, the reaction mixture was diluted with water and extracted with EtOAc. The organic layer was washed with water, brine, dried over Na2SO4 and concentrated. The crude product was directly used in the next step without further purification.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was directly used in the next step without further purification

Sources & evidence

ORD record
ord-5de4cbd9dc904e6b91692510a37222cd
Source dataset
uspto-grants-2014_06
Patent number
US08741925B2

Reaction notes

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