Water → Benzenamine, 4-bromo-N-methyl-

HRID 1978627Notes

Reaction equation

HRID 1978627 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:9]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:9][C:6]1[CH:7]=[CH:8][C:3]([NH:2][CH3:1])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7515N-MethylanilineHCID 67184N-bromobutanimide

Product 1

HCID 2757052Benzenamine, 4-bromo-N-methyl-Yield 104.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of N-methylaniline (10.0 g) in DMF (100 ml) was added dropwise a solution of at room temperature N-bromosuccinimide (16.6 g) in DMF (100 ml), and the mixture was stirred at room temperature for 20 hours. The reaction mixture was added to water, and the mixture was extracted with diethylether. The organic layer was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure to give pale yellow oil of 4-bromo-N-methylaniline (18.18 g).

Workup

  1. extractionthe mixture was extracted with diethylether
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-35a5d8e10fcc4a898824e32d138564e3
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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