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

HRID 983525Notes

Reaction equation

HRID 983525 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[CH2:9](Cl)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 72442-BromophenolHCID 7503Benzyl ChlorideHCID 11430Potassium Carbonate

Product 1

HCID 5618281-(Benzyloxy)-2-bromobenzeneYield 94.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 35 g of 1-bromo-2-hydroxybenzene, 30.5 g of benzyl chloride and 50 g of K2CO3 in 500 ml of acetone is refluxed for 12 hours. The reaction mixture is concentrated under vacuum, the residue is taken up in a water/EtOAc mixture, the organic phase is washed with 1N NaOH solution and with water and dried over Na2SO4, and the solvent is evaporated off under vacuum. The resulting oil is distilled under reduced pressure to give 50.3 g of the expected product, b.p.=155° C. at 40 Pa.

Workup

  1. temperatureis refluxed for 12 hours
  2. concentrationThe reaction mixture is concentrated under vacuum
  3. washthe organic phase is washed with 1N NaOH solution and with water
  4. dry with materialdried over Na2SO4
  5. customthe solvent is evaporated off under vacuum
  6. distillationThe resulting oil is distilled under reduced pressure

Sources & evidence

ORD record
ord-b8ade4e6503a427ab6350491b97258f8
Source dataset
uspto-grants-2005_03
Patent number
US06864277B2

Reaction notes

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