Benzyl Bromide → 1-Bromo-4-phenylmethoxybenzene

HRID 2250973Notes

Reaction equation

HRID 2250973 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.C(OCC)(=O)C>[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

6

Reactant 3

HCID 7498Benzyl BromideHCID 78084-BromophenolHCID 11430Potassium Carbonate

Product 1

HCID 1388351-Bromo-4-phenylmethoxybenzene

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Bromophenol (2 g, 0.0116 mol) in acetone (40 mL) was treated with potassium carbonate anhydrous (1.91 g, 1.2 equivalents) and benzyl bromide (1.44 mL, 1.05 equivalents). The reaction was refluxed under a nitrogen atmosphere. After 5-6 hours reflux, the reaction was cooled to room temperature and diluted with an equal volume of ethyl acetate. This solution was washed with water, dried over anhydrous magnesium sulfate and evaporated to dryness. A white fluffy solid was obtained. Yield=2.36 g (73%).

Workup

  1. temperatureThe reaction was refluxed under a nitrogen atmosphere
  2. temperatureAfter 5-6 hours reflux
  3. washThis solution was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated to dryness
  6. customA white fluffy solid was obtained

Sources & evidence

ORD record
ord-d06f43153be5413b9dba78e8a3777780
Source dataset
uspto-grants-2008_01
Patent number
US07319041B2

Reaction notes

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