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

HRID 1529649Notes

Reaction equation

HRID 1529649 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-0527ec3484594c0e95d744a5307ebb24
Source dataset
uspto-grants-2015_07
Patent number
US09090619B2

Reaction notes

Loading…