Benzyl Bromide → 1-Bromo-4-phenylmethoxybenzene

HRID 1245147Notes

Reaction equation

HRID 1245147 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[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(C)=O>[CH2:15]([O:8][C:5]1[CH:6]=[CH:7][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 78084-BromophenolHCID 11430Potassium Carbonate

Product 1

HCID 1388351-Bromo-4-phenylmethoxybenzeneYield 79%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Bromophenol (100 g, 0.587 mol) was dissolved in acetone (1100 ml), anhydrous potassium carbonate (159.53 g, 1.156 mmol) and benzyl bromide (103.78 g, 0.607 mol) were successively added thereto and the mixture was heated to reflux for 3 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The resulting crude product was recrystallized from hexane to give the title compound (120.76 g, 0.459 mol, 79%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting crude product was recrystallized from hexane

Sources & evidence

ORD record
ord-087b4a7ea7be48dfb0bd0d66b440f52f
Source dataset
uspto-grants-2006_10
Patent number
US07122543B2

Reaction notes

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