Water → 1-(Benzyloxy)-4-bromo-2-fluorobenzene

HRID 2276841Notes

Reaction equation

HRID 2276841 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CN(C)C=O>[CH2:16]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[F:9])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27249814-Bromo-2-fluorophenol

Product 1

HCID 187574911-(Benzyloxy)-4-bromo-2-fluorobenzeneYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen stream, 4-bromo-2-fluorophenol (14.9 g, 78 mmol) and potassium carbonate (13.0 g, 94 mmol) were dissolved in N,N-dimethylformamide (100 mL), followed by addition of benzyl bromide (10.2 mL, 86 mmol), and the mixture was stirred overnight at room temperature. Water was added to the reaction solution, and the solvent was concentrated under reduced pressure. The aqueous phase was extracted with ethyl acetate. The extracted solution was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue obtained was purified by column chromatography (ethyl acetate/hexane:0/100-5/95) to give the title compound (21.9 g, 100%).

Workup

  1. concentrationthe solvent was concentrated under reduced pressure
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. dry with materialThe extracted solution was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue obtained
  6. customwas purified by column chromatography (ethyl acetate/hexane:0/100-5/95)

Sources & evidence

ORD record
ord-fb095c1144f34faf897511f6d5b31d28
Source dataset
uspto-grants-2015_09
Patent number
US09133140B2

Reaction notes

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