Benzyl Bromide → 1-Bromo-4-phenylmethoxybenzene

HRID 1830207Notes

Reaction equation

HRID 1830207 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 (1,100 ml) and after adding thereto in sequence anhydrous potassium carbonate (159.53 g, 1.156 mmol) and benzyl bromide (103.78 g, 0.607 mol), the solution was refluxed under heating for 3 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The obtained crude product was recrystallized (the recrystallization operation was performed using hexane as a solvent) to obtain the titled compound (120.76 g, 0.459 mol, 79%).

Workup

  1. additionafter adding
  2. temperatureunder heating for 3 hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe obtained crude product
  6. customwas recrystallized (the recrystallization operation

Sources & evidence

ORD record
ord-096d884180ab47229c9149d370dc27db
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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