Phenacyl bromide → Methanone, 2-benzofuranylphenyl-

HRID 256407Notes

Reaction equation

HRID 256407 reaction equation
[O-]CC.[Na+].[Na].[CH:6](=O)[C:7]1[C:8](=[CH:10][CH:11]=[CH:12][CH:13]=1)[OH:9].Br[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:18]>C(O)C.CN(C)C=O>[C:17]([C:16]1[O:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[CH:6]=1)(=[O:18])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 6259Phenacyl bromideHCID 6998SalicylaldehydeHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 95808Methanone, 2-benzofuranylphenyl-Yield 34.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of sodium ethoxide prepared from 28 g sodium metal and 500 ml absolute ethanol was added 122 g (1 mole) salicylaldehyde and 200 ml dimethylformamide. The mixture was heated to 80° C. Then 200 g (1 mole) alpha-bromoacetophenone was added in small portions. The mixture was stirred at reflux for 1.5 hours after which the ethanol was distilled. The residue was cooled and partitioned between 750 ml water and 750 ml ethyl acetate. The organic layer was washed twice with 400 ml portions of 1N sodium hydroxide, water (2×300 ml), dried (Na2SO4), concentrated to one-third volume, filtered to remove precipitated product which was washed with ethyl ether to yield 75.8 g of 2-benzoylbenzo(b)furan as pink crystals, m.p. 88°-90° C.

Workup

  1. distillationwas distilled
  2. temperatureThe residue was cooled
  3. custompartitioned between 750 ml water and 750 ml ethyl acetate
  4. washThe organic layer was washed twice with 400 ml portions of 1N sodium hydroxide, water (2×300 ml)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated to one-third volume
  7. filtrationfiltered
  8. customto remove
  9. customprecipitated product which
  10. washwas washed with ethyl ether

Sources & evidence

ORD record
ord-e8fe0c16a24a4725ab5a694551ac1e50
Source dataset
uspto-grants-1987_10
Patent number
US04703052

Reaction notes

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