4-Bromophenacyl bromide → 1-(4-Bromophenyl)-2-fluoroethan-1-one

HRID 394875Notes

Reaction equation

HRID 394875 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)=[O:4].[F-:12].[K+].C1OCCOCCOCCOCCOCCOC1>C(#N)C>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][F:12])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 74544-Bromophenacyl bromideHCID 2855718-Crown-6HCID 522689Potassium Fluoride

Product 1

HCID 100362781-(4-Bromophenyl)-2-fluoroethan-1-oneYield 102.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-bromo-1-(4-bromophenyl)-1-ethanone (8.54 g, 30.7 mmol), potassium fluoride (8.92 g, 153 mmol) and 18-crown-6 ether (4.06 g, 15.3 mmol) in acetonitrile (170 ml) was refluxed for 7 hr. After evaporation, the mixture was dissolved in ethyl acetate (300 ml), washed with water (100 ml×2), and dried over magnesium sulfate. Removal of solvent gave 6.8 g of brown solid, which was chromatographed on a column of silica gel (600 g) eluting with ethyl acetate/hexane (1:10) to afford 5.00 g (75%) of the title compound as a pale yellow solid.

Workup

  1. temperaturewas refluxed for 7 hr
  2. customAfter evaporation
  3. dissolutionthe mixture was dissolved in ethyl acetate (300 ml)
  4. washwashed with water (100 ml×2)
  5. dry with materialdried over magnesium sulfate
  6. customRemoval of solvent

Sources & evidence

ORD record
ord-e383e9eb5ec74fb6bdf7e514782f51bb
Source dataset
uspto-grants-2003_08
Patent number
US06603008B1

Reaction notes

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