Water → 4-bromo-N-ethylaniline

HRID 1978625Notes

Reaction equation

HRID 1978625 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].[Br:10]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:10][C:7]1[CH:8]=[CH:9][C:4]([NH:3][CH2:1][CH3:2])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7670N-EthylanilineHCID 67184N-bromobutanimide

Product 1

HCID 117456564-bromo-N-ethylanilineYield 103.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of N-ethylaniline (10.0 g) in DMF (50 ml) was added dropwise at room temperature a solution of N-bromosuccinimide (14.69 g) in DMF (100 ml), and the mixture was stirred at room temperature for 19 hours. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried with magnesium sulfate and concentrated under reduced pressure to give pale yellow oil of 4-bromo-N-ethylaniline (17.08 g).

Workup

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

Sources & evidence

ORD record
ord-21e5c4ce4ede44daa0f49cff92f99c2c
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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