Phenacyl bromide → Phenacyl phenyl sulfide

HRID 2194679Notes

Reaction equation

HRID 2194679 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[C:17]1([SH:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)C>[C:5]1([C:3](=[O:4])[CH2:2][S:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 7969ThiophenolHCID 11430Potassium Carbonate

Product 1

HCID 85338Phenacyl phenyl sulfideYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-bromoacetophenone (10 g) and potassium carbonate (7.1 g) in ethanol (150 mL) was added thiophenol (5.2 mL) under ice-cooling, and the mixture was stirred at room temperature for 12 hr. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine in this order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=15:1) to give the title compound as yellow crystals (yield 11 g, yield 98%).

Workup

  1. temperaturecooling
  2. filtrationInsoluble material was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine in this order
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=15:1)

Sources & evidence

ORD record
ord-5df9c7111ae94416bced9741ca2d4271
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

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