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

HRID 1830206Notes

Reaction equation

HRID 1830206 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) and after adding thereto in sequence anhydrous potassium carbonate (80 g, 0.580 mmol) and benzyl bromide (59 g, 0.345 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 recrystallized (the recrystallization operation was performed twice using hexane as a solvent) to obtain the titled compound (45.0 g, 0.171 mol, 59%).

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 recrystallized (the recrystallization operation

Sources & evidence

ORD record
ord-35252cb894654cf69c030c5f80852c14
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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