Benzyl Bromide → HCID 18414640, compound

HRID 991587Notes

Reaction equation

HRID 991587 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH2:9][CH2:10][CH3:11])[CH:3]=1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:4]([CH2:9][CH2:10][CH3:11])[CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 221345104-Bromo-2-propylphenol

Product 1

HCID 18414640HCID 18414640, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a 100 ml acetone solution of 4-bromo-2-propylphenol 5.4 g (25.1 mol) and benzyl bromide 5.6 g (32.7 mmol) was added potassium carbonate 5.2 g (37.6 mmol). Resulting suspension was stirred under reflux temperature for overnight. Acetone was removed under reduced pressure, diluted with ethyl acetate and water. Organic phase was separated. Aqueous phase was extracted with ethyl acetate twice. The combined organic phases were dried over anhydrous sodium sulfate, filtered, concentrated, chromatographed on silica gel (hexanes: t-butyl methyl ether) to give 6.96 g of benzyl 4-bromo-2-propylphenyl ether as colorless oil.

Workup

  1. customResulting suspension
  2. temperatureunder reflux temperature for overnight
  3. customAcetone was removed under reduced pressure
  4. additiondiluted with ethyl acetate and water
  5. customOrganic phase was separated
  6. extractionAqueous phase was extracted with ethyl acetate twice
  7. dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customchromatographed on silica gel (hexanes: t-butyl methyl ether)

Sources & evidence

ORD record
ord-823dea59bfe942c895ccd52a42cd59a8
Source dataset
uspto-grants-2002_10
Patent number
US06465497B2

Reaction notes

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