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

HRID 2378194Notes

Reaction equation

HRID 2378194 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=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>[CH2:2]([O:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([Br:9])[CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=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 bromomethylbenzene (24.39 g, 143 mmol), 3-bromophenol (24.92 g, 144 mmol) in acetone (20 ml) was added potassium carbonate (59.72 g, 430 mmol). The suspension was refluxed overnight and then evaporated. To the residue was added H2O (100 ml) and extracted with EtOAc (3×80 ml). The combined EtOAc extracts were back washed with Na2CO3 and then dried over MgSO4, filtered and evaporated to get an off-white solid, which was purified via flash column chromatography (10% CH2Cl2 in hexane) to give 1-benzyloxy-3-bromo-benzene as a white solid (10 g, 67%): 1HNMR (DMSO-d6) 7.46-7.00 (m, 9H, Ar), 5.12 (s, 2H, CH2). The product was carried over to the next step.

Workup

  1. temperatureThe suspension was refluxed overnight
  2. customevaporated
  3. additionTo the residue was added H2O (100 ml)
  4. extractionextracted with EtOAc (3×80 ml)
  5. washThe combined EtOAc extracts were back washed with Na2CO3
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customto get an off-white solid, which
  10. customwas purified via flash column chromatography (10% CH2Cl2 in hexane)

Sources & evidence

ORD record
ord-fe8f641780b2495f99a6c7bebf3aab0f
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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