2-Bromophenol → 1-(Benzyloxy)-2-bromobenzene

HRID 1245148Notes

Reaction equation

HRID 1245148 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].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:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 72442-BromophenolHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 5618281-(Benzyloxy)-2-bromobenzeneYield 40%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Bromophenol (50.0 g, 0.289 mol) was dissolved in acetone (400 ml), anhydrous potassium carbonate (79.89 g, 0.578 mmol) and benzyl bromide (59.32 g, 0.347 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 product was purified by silica gel column chromatography (hexane:AcOEt=95:5) to give the title compound (30.0 g, 0.114 mol, 40%).

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 product was purified by silica gel column chromatography (hexane:AcOEt=95:5)

Sources & evidence

ORD record
ord-dcd8325e76324bcb9357e7ce3069bc23
Source dataset
uspto-grants-2006_10
Patent number
US07122543B2

Reaction notes

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