Water → n,n-dibenzyl-4-bromoaniline

HRID 1058646Notes

Reaction equation

HRID 1058646 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>CN(C)C=O>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 78074-BromoanilineHCID 24758Sodium hydride

Product 1

HCID 285423n,n-dibenzyl-4-bromoanilineYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In an argon atmosphere, 4-bromoaniline (344 mg, 2.00 mmol) was dissolved in dimethylformamide (5 mL), and to the solution were added sodium hydride (200 mg, 5.00 mmol) and benzyl bromide (0.52 mL, 4.4 mmol) under ice-cooling, followed by stirring at room temperature for 11 hours. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was recrystallized from ethyl acetate/hexane to obtain 4-bromo-N,N-dibenzylaniline (442 mg, 63%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-0668325c957e48bfba01301a7f3f3a31
Source dataset
uspto-grants-2003_02
Patent number
US06518268B1

Reaction notes

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