Benzyl Bromide → HCID 67058419, compound

HRID 269588Notes

Reaction equation

HRID 269588 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[OH:9].[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 132842722-Bromo-5-chlorophenol

Product 1

HCID 67058419HCID 67058419, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-bromo-5-chlorophenol (3.93 g, 18.94 mmol), benzyl bromide (3.42 g, 20 mmol) and potassium carbonate (10 g, 72.46 mmol) in acetone (80 ml) was stirred and refluxed for 3 hours then cooled, evaporated and dissolved in ether/water. The organic phase was dried (magnesium sulphate) evaporated and purified by chromatography on silica eluting with ethyl acetate/iso-hexane (1:99) to give 5.51 g of white solid.

Workup

  1. temperaturerefluxed for 3 hours
  2. temperaturethen cooled
  3. customevaporated
  4. dissolutiondissolved in ether/water
  5. dry with materialThe organic phase was dried (magnesium sulphate)
  6. customevaporated
  7. custompurified by chromatography on silica eluting with ethyl acetate/iso-hexane (1:99)

Sources & evidence

ORD record
ord-d9292a6cf0e542dea94b01ff32c6b94e
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Reaction notes

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