Benzyl Bromide → 1-Benzyloxy-4-bromo-2,5-difluorobenzene

HRID 2253032Notes

Reaction equation

HRID 2253032 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([Br:9])=[CH:4][C:3]=1[F:10].C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(=O)CC>[CH2:17]([O:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([Br:9])=[CH:4][C:3]=1[F:10])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 70180424-Bromo-2,5-difluorophenol

Product 1

HCID 580861601-Benzyloxy-4-bromo-2,5-difluorobenzene

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of 21 g of 1-hydroxy-4-bromo-2,5-difluoro-benzene in 2-butanone (300 ml) and was added potassium carbonate (20.8 g) and benzylbromide (24 mL). The reaction mixture was boiled while stirring for 1.5 hours. After cooling to room temperature the mixture was partitioned between ethyl acetate and water. Organic phases were pooled, dried with MgSO4 and concentrated in vacuo. The residue was then purified by column chromatography (heptane/silica gel) to give 25.3 g of the title compound.

Workup

  1. customwas partitioned between ethyl acetate and water
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was then purified by column chromatography (heptane/silica gel)

Sources & evidence

ORD record
ord-2de12e4942cb43d39b43ce1a91fa6fac
Source dataset
uspto-grants-2008_01
Patent number
US07323466B2

Reaction notes

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