Benzyl Bromide → 1-(Benzyloxy)-3-bromobenzene

HRID 1245146Notes

Reaction equation

HRID 1245146 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=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:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][CH:5]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 115633-Bromophenol

Product 1

HCID 27566381-(Benzyloxy)-3-bromobenzeneYield 59.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-Bromophenol (50 g, 0.289 mol) was dissolved in acetone (500 ml), anhydrous potassium carbonate (80 g, 0.580 mmol) and benzyl bromide (59 g, 0.345 mol) were successively added thereto and the mixture was heated to reflux for 3 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The resulting crude reaction product was recrystallized (hexane was used as a solvent and the recrystallization operation was carried out twice) to give the title compound (45.0 g, 0.171 mol, 59%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting crude reaction product
  6. customwas recrystallized (hexane

Sources & evidence

ORD record
ord-752dd3623a774ae285e3f2c942f88e2e
Source dataset
uspto-grants-2006_10
Patent number
US07122543B2

Reaction notes

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