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

HRID 1830208Notes

Reaction equation

HRID 1830208 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) and after adding thereto in sequence anhydrous potassium carbonate (79.89 g, 0.578 mmol) and benzyl bromide (59.32 g, 0.347 mol), the solution was refluxed under heating for 3 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (hexane:AcOEt=95:5) to obtain the titled compound (30.0 g, 0.114 mol, 40%).

Workup

  1. additionafter adding
  2. temperatureunder heating for 3 hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe obtained crude product
  6. customwas purified by silica gel column chromatography (hexane:AcOEt=95:5)

Sources & evidence

ORD record
ord-9132de3064e2494da6c97bec8e581639
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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