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

HRID 1822335Notes

Reaction equation

HRID 1822335 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C=O)C>[CH2:15]([O:8][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][CH:5]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 115633-Bromophenol

Product 1

HCID 27566381-(Benzyloxy)-3-bromobenzeneYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-bromophenol (10.0 g, 57.8 mmol) and 325 mesh potassium carbonate (8.79 g, 63.6 mmol) in DMF (100 mL) is treated dropwise with benzyl bromide (9.89 g, 57.8 mmol) and then stirred 20 hours at rt under N2. The reaction is filtered, and the filtrate is acidified with 1 N HCl. The mixture is then diluted with water and extracted with Et2O. The organic layer is dried (Na2SO4), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using 10/1 hexanes/ethyl acetate to afford 14.55 g (96%) of the titled compound. Rf=0.86 (4/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3).

Workup

  1. filtrationThe reaction is filtered
  2. additionThe mixture is then diluted with water
  3. extractionextracted with Et2O
  4. dry with materialThe organic layer is dried (Na2SO4)
  5. customthe solvent is removed in vacuo
  6. customto afford crude product that
  7. customis absorbed on silica gel
  8. custompurified by flash chromatography

Sources & evidence

ORD record
ord-9ad6ff6f61e547a9880e7c031d54dff2
Source dataset
uspto-grants-2009_10
Patent number
US07608639B2

Reaction notes

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