Hydrochloric Acid → 1-(Benzyloxy)-3-bromo-5-methylbenzene

HRID 1787732Notes

Reaction equation

HRID 1787732 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CC(C)=O>[CH2:10]([O:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([Br:1])[CH:3]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 126484093-Bromo-5-methylphenol

Product 1

HCID 689015981-(Benzyloxy)-3-bromo-5-methylbenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-bromo-5-methylphenol [(40.7 g, 218 mmol) J. Amer. Chem. Soc., 2003, 125, 7792)], benzyl bromide (28.6 mL, 239 mmol) and potassium carbonate (90.2 g, 653 mmol) in acetone (1 L) was heated under reflux for 2 hours. The cooled reaction mixture was then acidified with 2M hydrochloric acid and the aqueous layer was extracted with ethyl acetate. The organic solution was washed with brine (×3), dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a red oil in quantitative yield.

Workup

  1. temperatureunder reflux for 2 hours
  2. customThe cooled reaction mixture
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe organic solution was washed with brine (×3)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f091a658fc9f4476afd56d5fa7dad279
Source dataset
uspto-grants-2009_03
Patent number
US07511057B2

Reaction notes

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