Benzyl Bromide → 2-(Benzyloxy)-1-bromo-4-fluorobenzene

HRID 554524Notes

Reaction equation

HRID 554524 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=1[OH:15].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.S([O-])(O)(=O)=O.[K+]>CN(C=O)C>[CH2:16]([O:15][C:9]1[CH:10]=[C:11]([F:14])[CH:12]=[CH:13][C:8]=1[Br:7])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 516920Potassium bisulfateHCID 27246002-Bromo-5-fluorophenol

Product 1

HCID 192614712-(Benzyloxy)-1-bromo-4-fluorobenzeneYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (2.61 g, 18.8 mmol) was added to a solution of 2-bromo-5-fluorophenol (3.0 g, 15.7 mmol) in DMF (15.7 mL) and the mixture was stirred in a nitrogen stream at room temperature for 15 minutes. To this solution, benzyl bromide (2.69 g, 15.7 mmol) was added dropwise at the same temperature and the mixture solution was stirred at the same temperature overnight. To the reaction mixture was added a potassium hydrogensulfate aqueous solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduce pressure. The obtained residue was purified by silica gel column chromatography (developing solution=n-hexane) to obtain the title compound (4.31 g, 98%) as a colorless oil.

Workup

  1. stirringthe mixture solution was stirred at the same temperature overnight
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  4. dry with materialdried (anhydrous magnesium sulfate)
  5. distillationthe solvent was distilled
  6. customThe obtained residue was purified by silica gel column chromatography (developing solution=n-hexane)

Sources & evidence

ORD record
ord-6e92c57756a4428bb22be802fe0768c3
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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