N-bromobutanimide → 2-Bromo-4-(tert-butyl)aniline
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
Product 1
Reagents, catalysts & solvents 2
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
- extractionextracted with EtOAc
- washThe organic layer was washed with water, brine
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customThe crude product was directly used in the next step without further purification
Sources & evidence
- ORD record
- ord-57d8dfbedc054c4db140146be991bfd7
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08748612B2
Reaction notes
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