Benzyl Bromide → 1-Bromo-4-phenylmethoxybenzene

HRID 2212557Notes

Reaction equation

HRID 2212557 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH2:9](Br)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 78084-BromophenolHCID 10796Cesium carbonate

Product 1

HCID 1388351-Bromo-4-phenylmethoxybenzene

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-Bromophenol (3.9 g, 22.41 mmol), benzyl bromide (4.6 g, 26.9 mmol), and cesium carbonate (89.6 mmol) were combined in DMSO (30 mL) under nitrogen at room temperature. The reaction was stirred for 24 h, filtered to remove the solids, and then partitioned between ethyl acetate and water. The organic layer was washed with water, 1 N HCl, and brine; dried over magnesium sulfate; and, concentrated to give a semi-solid. The product was crystallized from hexanes to give 1-bromo-4-benzyloxy-benzene as an off white powder (4.3 g, 75%). MS found: (M+H)+=263, 265.

Workup

  1. filtrationfiltered
  2. customto remove the solids
  3. custompartitioned between ethyl acetate and water
  4. washThe organic layer was washed with water, 1 N HCl, and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationand, concentrated
  7. customto give a semi-solid
  8. customThe product was crystallized from hexanes

Sources & evidence

ORD record
ord-74dfdb5886494b639626d45b0448131f
Source dataset
uspto-grants-2006_09
Patent number
US07102008B2

Reaction notes

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