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

HRID 1197840Notes

Reaction equation

HRID 1197840 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-fluorobenzeneYield 57%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Sodium hydride (50% w/w dispersion in mineral oil, 12.4 g) was added portionwise to a mixture of benzyl alcohol (26.7 ml) and DMA (500 ml) and the mixture was stirred at ambient temperature for 1 hour. 1-Bromo-3,5-difluorobenzene (50 g) was added carefully to control the vigour of the ensuing exothermic reaction. The mixture was stirred at ambient temperature for 2 hours and the solvent was evaporated. The residue was partitioned between methylene chloride and water and the organic phase was washed with water (4×50 ml), dried (MgSO4) and evaporated. The residue was purified by distillation to give 3-benzyloxy-1-bromo-5-fluorobenzene (41.8 g, 57%), as a colourless liquid (b.p. 124°-130° C. at 0.3 mm Hg).

Workup

  1. customthe vigour of the ensuing exothermic reaction
  2. stirringThe mixture was stirred at ambient temperature for 2 hours
  3. customthe solvent was evaporated
  4. customThe residue was partitioned between methylene chloride and water
  5. washthe organic phase was washed with water (4×50 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. distillationThe residue was purified by distillation

Sources & evidence

ORD record
ord-c413883554014b5ea61f6b2e6c3881ba
Source dataset
uspto-grants-1994_01
Patent number
US05278177

Reaction notes

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