Benzyl Bromide → 1-Bromo-4-phenylmethoxybenzene

HRID 254134Notes

Reaction equation

HRID 254134 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-a1cd9b1875ed4b24b8af85eae921206d
Source dataset
uspto-grants-2011_01
Patent number
US07875467B2

Reaction notes

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