N-bromobutanimide → 2-Bromo-4-benzylaniline

HRID 1097165Notes

Reaction equation

HRID 1097165 reaction equation
[CH2:1]([C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C(=O)N([Br:22])C(=O)C1>CN(C)C=O>[Br:22][C:13]1[CH:14]=[C:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:9]=[CH:10][C:11]=1[NH2:12]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 136914Benzenamine, 4-(phenylmethyl)-

Product 1

HCID 193811412-Bromo-4-benzylaniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The commercially available 4-benzyl aniline can be selectively brominated at the ortho position using n-bromosuccinimide in dimethylformamide to give the desired 2-bromo-4-benzyl aniline.

Sources & evidence

ORD record
ord-2c75c346ae5042198ca61fbdbf302531
Source dataset
uspto-grants-2012_03
Patent number
US08142909B2

Reaction notes

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