N-bromobutanimide → 3-Bromo-4-(dimethylamino)benzonitrile

HRID 2252302Notes

Reaction equation

HRID 2252302 reaction equation
[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.[Br:12]N1C(=O)CCC1=O>ClCCl>[Br:12][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:3]=1[N:2]([CH3:11])[CH3:1])[C:7]#[N:8]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 709674-(Dimethylamino)benzonitrile

Product 1

HCID 224774413-Bromo-4-(dimethylamino)benzonitrileYield 94.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-dimethylaminobenzonitrile (2.92 g, 20 mmol) and N-bromosuccinimide (3.56 g, 20 mmol) in dichloromethane (50 mL) was stirred at room temperature overnight. The solution was washed with water (20 mL), dried over magnesium sulfate and concentrated to afford 3-bromo-4-dimethylaminobenzonitrile as a white solid (4.27 g).

Workup

  1. washThe solution was washed with water (20 mL)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3c3838d256fe4aeb997ad32a2f42441e
Source dataset
uspto-grants-2008_01
Patent number
US07321041B2

Reaction notes

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