Benzyl Bromide → HCID 11955083, compound

HRID 967706Notes

Reaction equation

HRID 967706 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][C:19]=1[F:25])=[O:17]>C(O)C>[CH2:7]([O:24][C:21]1[CH:22]=[CH:23][C:18]([C:16](=[O:17])[CH3:15])=[C:19]([F:25])[CH:20]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27249122'-Fluoro-4'-hydroxyacetophenone

Product 1

HCID 11955083HCID 11955083, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Potassium carbonate (5.5 g, 40.0 mmol) and benzyl bromide (4.6 ml, 38.9 mmol) were added to a solution of 2-fluoro-4-hydroxyacetophenone (5.0 g, 32.4 mmol) in ethanol (50 ml), and the mixture was heated at reflux temperature for 16 h. The reaction mixture was evaporated to a residue to which 2 N HCl (100 ml) was added. This mixture was extracted with ethyl ether (3×60 ml) and the combined extracts were washed with brine (10 ml), dried (MgSO4), and evaporated to a residue, which was crystallized from ethyl acetate (7.4 g, 93%): MS(ES) m/z 245 (M+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 16 h
  3. customThe reaction mixture was evaporated to a residue to which 2 N HCl (100 ml)
  4. additionwas added
  5. extractionThis mixture was extracted with ethyl ether (3×60 ml)
  6. washthe combined extracts were washed with brine (10 ml)
  7. dry with materialdried (MgSO4)
  8. customevaporated to a residue, which
  9. customwas crystallized from ethyl acetate (7.4 g, 93%)

Sources & evidence

ORD record
ord-4a44e5947f314a6e9e669f9fd2cb954c
Source dataset
uspto-grants-2005_10
Patent number
US06956036B1

Reaction notes

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