Benzyl Bromide → Methyl 4-(benzyloxy)-3-bromobenzoate

HRID 1662375Notes

Reaction equation

HRID 1662375 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].Br[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O>[CH2:14]([O:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[Br:1])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 4778958Methyl 3-bromo-4-hydroxybenzoate

Product 1

HCID 23111814Methyl 4-(benzyloxy)-3-bromobenzoate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 66.6E (53.2 g, 230 mmol) in DMSO (45.0 mL) was added 1-(bromomethyl)benzene (35.6 mL, 299 mmol). After cooling in an ice water bath, cesium carbonate (128 g, 391 mmol) was carefully added to the mixture, and the mixture was allowed to warm to room temperature. After overnight stirring, the mixture was diluted with water and extracted three times with EtOAc. The organic layers were combined and then washed with brine. After drying over anhydrous magnesium sulfate and filtration, the organic solvent was removed under reduced pressure to yield 66.11C as a white solid.

Workup

  1. temperatureAfter cooling in an ice water bath
  2. extractionextracted three times with EtOAc
  3. washwashed with brine
  4. dry with materialAfter drying over anhydrous magnesium sulfate and filtration
  5. customthe organic solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-80d560b630624801810739280910d14d
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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