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

HRID 2378315Notes

Reaction equation

HRID 2378315 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:9][C:10]1[CH:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([Br:9])[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 115633-Bromophenol

Product 1

HCID 27566381-(Benzyloxy)-3-bromobenzeneYield 67%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of benzyl bromide (24.39 g, 142.6 mmol) and 3-bromo phenol (24.92 g, 144 mmol) in 20 mL of fresh acetone was added potassium carbonate (59.72 g, 432 mmol). The suspension was refluxed overnight. The mixture was evaporated and added water (100 mL), extracted with EtOAc (3×80 mL). The combined EtOAc extracts were back washed with water (100 mL), dried over MgSO4, filtered and evaporated to give 1-benzyloxy-3-bromo-benzene as an off-white solid (10.0 g, 67% yield): 1H NMR (DMSO-d6) δ 5.12 (s, 2H, CH2), 7.00-7.46 (m, 9H, Ar). The product was used in the next step without further purification.

Workup

  1. temperatureThe suspension was refluxed overnight
  2. customThe mixture was evaporated
  3. additionadded water (100 mL)
  4. extractionextracted with EtOAc (3×80 mL)
  5. washThe combined EtOAc extracts were back washed with water (100 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-4adf87e2a9704a2686a881a546cc5910
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

Loading…