Benzyl Bromide → n,n-dibenzyl-4-bromoaniline

HRID 1842912Notes

Reaction equation

HRID 1842912 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CC#N>[CH2:15]([N:6]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:5]1[CH:7]=[CH:8][C:2]([Br:1])=[CH:3][CH:4]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 78074-BromoanilineHCID 11430Potassium Carbonate

Product 1

HCID 285423n,n-dibenzyl-4-bromoanilineYield 87.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 4-bromoaniline (500 mg, 2.92 mmol, 1.0 eq) and K2CO3 (1.21 g, 8.76 mmol, 3.0 eq) in CH3CN (10 mL) was added benzyl bromide (1.24 g, 7.30 mmol, 2.5 eq) and the mixture stirred for 16 h at 80° C. and cooled to RT. K2CO3 was filtered out, the filtrate concentrated, the resulting crude product was purified by CC using EtOAc/PE (1:19) to get N,N-dibenzyl-4-bromoaniline (900 mg, 87%; TLC system: EtOAc/PE (3:7), Rf: 0.7).

Workup

  1. temperaturecooled to RT
  2. filtrationK2CO3 was filtered out
  3. concentrationthe filtrate concentrated
  4. customthe resulting crude product was purified by CC

Sources & evidence

ORD record
ord-d43805462f01411f9ee687a560a3b6d4
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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