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Benzyl Bromide → 1-Bromo-4-phenylmethoxybenzene

HRID 11201
Notes
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Reaction equation

HRID 11201 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 78084-BromophenolHCID 11430Potassium Carbonate

Product 1

HCID 1388351-Bromo-4-phenylmethoxybenzene

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolvent
HCID 8857
Ethyl Acetate
Solvent

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-9c38a67482a74a60b22a9dd04f69b8a7
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07097995B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes