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

HRID 1958532Notes

Reaction equation

HRID 1958532 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-3d65d5a022404ccb828faef9f73cf80f
Source dataset
uspto-grants-2013_04
Patent number
US08410132B2

Reaction notes

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