Benzyl Chloride → 4-Bromo-2,6-difluoro-1-(benzyloxy)benzene

HRID 477413

Reaction equation

HRID 477413 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([OH:9])=[C:4]([F:10])[CH:3]=1.[CH2:11](Cl)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>>[CH2:11]([O:9][C:5]1[C:6]([F:8])=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[F:10])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 27362924-Bromo-2,6-difluorophenol

Product 1

HCID 142076414-Bromo-2,6-difluoro-1-(benzyloxy)benzene

Procedure

A stirred mixture of 4-bromo-2,6-difluorophenol (36 g, 0.172 mole), benzylchloride (21.77 g, 0.172 mole), and potassium carbonate (25 g, 0.18 mole) in demethylformamide (300 ml) was heated at 80°-90° for four hours. After cooling, the solvent was evaporated and ether added to the residue. The insoluble inorganic salts were removed by filtration, and solvent evaporated from the filtrate. The oily residue was subjected to bulb-to-bulb vacuum distillation on Kugelrohr apparatus to give the desired product as a nearly colorless oil (41 g, 80 percent): R.I.=1.5602 @25° C.; NMR (CDCl3) was consistent with the assigned structure.

Workup

  1. temperaturewas heated at 80°-90° for four hours
  2. temperatureAfter cooling
  3. customthe solvent was evaporated
  4. additionether added to the residue
  5. customThe insoluble inorganic salts were removed by filtration, and solvent
  6. customevaporated from the filtrate
  7. distillationThe oily residue was subjected to bulb-to-bulb vacuum distillation on Kugelrohr apparatus

Sources & evidence

ORD record
ord-5f6f1a4f9b904e84b71428c8456e32ba
Source dataset
uspto-grants-1989_12
Patent number
US04888050

Linked notes

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