Benzyl Alcohol → 1-(Benzyloxy)-3-bromo-5-fluorobenzene

HRID 1377591Notes

Reaction equation

HRID 1377591 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Br:11][C:12]1[CH:17]=[C:16]([F:18])[CH:15]=[C:14](F)[CH:13]=1>CC(N(C)C)=O>[CH2:3]([O:10][C:14]1[CH:13]=[C:12]([Br:11])[CH:17]=[C:16]([F:18])[CH:15]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 1363131-Bromo-3,5-difluorobenzene

Product 1

HCID 112545161-(Benzyloxy)-3-bromo-5-fluorobenzene

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Sodium hydride (60% w/w dispersion in mineral oil) 10.3 g was added portion-wise to a solution of benzyl alcohol (28.8 ml) in dimethylacetamide (400 ml) and the mixture stirred at room temperature for about 1 hour. 1-Bromo-3,5-difluorobenzene (50 g) was added dropwise. The mixture was stirred at room temperature for about 2 hours and the solvent was evaporated in vacuo. The residue was partitioned between methylene chloride and water and the organic phase was washed with water, dried over sodium sulfate and evaporated to give 90 g of crude product which was purified on silica gel eluting with methylene chloride/hexanes to give 47.7 g of the title compound as an oil.

Workup

  1. stirringThe mixture was stirred at room temperature for about 2 hours
  2. customthe solvent was evaporated in vacuo
  3. customThe residue was partitioned between methylene chloride and water
  4. washthe organic phase was washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customto give 90 g of crude product which
  8. customwas purified on silica gel eluting with methylene chloride/hexanes

Sources & evidence

ORD record
ord-0fa73ded52f04288bc44b978189c8ed3
Source dataset
uspto-grants-1997_09
Patent number
US05665749

Reaction notes

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