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

HRID 2306180Notes

Reaction equation

HRID 2306180 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([O:8][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 115633-Bromophenol

Product 1

HCID 27566381-(Benzyloxy)-3-bromobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3-bromophenol (9.50 g, 54.9 mmol) in degassed DMF (150 mL) at 0° C., under argon, was added Cs2CO3 (35.8 g, 109 mmol). The resulting mixture was stirred for 1 hour, then benzyl bromide (10.3 g, 60.2 mmol) was added and stirring was continued for 2 hours at 0° C. The solvent was removed under reduced pressure, and the residue was partitioned between 20% aqueous NaOH (250 mL) and CHCl3 (500 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography on silica, eluting first with two column volumes of hexane, then with hexane—2% EtOAc to yield the desired product as a white solid.

Workup

  1. stirringstirring
  2. waitwas continued for 2 hours at 0° C
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was partitioned between 20% aqueous NaOH (250 mL) and CHCl3 (500 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash column chromatography on silica
  9. washeluting first with two column volumes of hexane

Sources & evidence

ORD record
ord-8f00a60af294458f88fb33e3eb057bc8
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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