Benzyl Bromide → 1-Bromo-4-phenylmethoxybenzene

HRID 2373102Notes

Reaction equation

HRID 2373102 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.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

7

Reactant 3

HCID 7498Benzyl BromideHCID 78084-BromophenolHCID 11430Potassium Carbonate

Product 1

HCID 1388351-Bromo-4-phenylmethoxybenzene

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

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

Workup

  1. temperatureThe reaction was refluxed under nitrogen
  2. temperatureAfter 5-6 hours of reflux
  3. customthe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness
  6. customto afford a white fluffy powder

Sources & evidence

ORD record
ord-7641f4b513be4a8195275046b45bb342
Source dataset
uspto-grants-2008_12
Patent number
US07459284B2

Reaction notes

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