2,6-Diethylaniline → 4-Bromo-2,6-diethylaniline

HRID 2041824Notes

Reaction equation

HRID 2041824 reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH3:11])[C:4]=1[NH2:5])[CH3:2].C1C(=O)N([Br:19])C(=O)C1>CN(C=O)C>[Br:19][C:8]1[CH:7]=[C:6]([CH2:10][CH3:11])[C:4]([NH2:5])=[C:3]([CH2:1][CH3:2])[CH:9]=1

Participants

4

Reactant 2

HCID 113692,6-DiethylanilineHCID 67184N-bromobutanimide

Product 1

HCID 6114524-Bromo-2,6-diethylanilineYield 51.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2,6-diethylaniline (7 g, 46.9 mmol) was dissolved in 50 mL of DMF in a round-bottom flask and cooled with an ice-water bath. N-bromosuccimide (NBS) (9.18 g, 51.6 mmol) was dissolved in 100 mL of DMF and added dropwise to the flask via a dropping funnel. The reaction was warmed slowly to room temperature and reacted overnight before it was quenched by ice water. The product was extracted with dichloromethane and washed with lithium chloride solution. After evaporating solvent, the residue was purified by silica gel column chromatography. 5.5 g (51.4% yield) of product was obtained.

Workup

  1. temperaturecooled with an ice-water bath
  2. additionadded dropwise to the flask via a dropping funnel
  3. customreacted overnight before it
  4. customwas quenched by ice water
  5. extractionThe product was extracted with dichloromethane
  6. washwashed with lithium chloride solution
  7. customAfter evaporating solvent
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-75046b22d67742aaad9e7df89e04651f
Source dataset
uspto-grants-2013_11
Patent number
US08586204B2

Reaction notes

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