Phenacyl bromide → Phenacyl phenyl sulfide

HRID 1415682Notes

Reaction equation

HRID 1415682 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[C:11]1([SH:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>N1C=CC=CC=1>[C:11]1([S:17][CH2:2][C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:4])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 7969Thiophenol

Product 1

HCID 85338Phenacyl phenyl sulfideYield 67.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 300 mL of pyridine was added a-bromoacetophenone (150 g, 750 mmol) and thiophenol (83 g, 750 mmol). The mixture was heated at reflux for six hours. The pyridine was evaporated and the residue dissolved in ethyl acetate. The ethyl acetate solution was washed exhaustively with 1 N sodium hydroxide, then with 1 N hydrochloric acid, dried over magnesium sulfate, filtered, and evaporated to yield a brown oil. The product was crystallized from ethanol at 0° C. to yield 116 g of the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for six hours
  3. customThe pyridine was evaporated
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washThe ethyl acetate solution was washed exhaustively with 1 N sodium hydroxide
  6. dry with materialwith 1 N hydrochloric acid, dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customto yield a brown oil
  10. customThe product was crystallized from ethanol at 0° C.

Sources & evidence

ORD record
ord-a2d7cc1c6e9c4a04b436aa176967140e
Source dataset
uspto-grants-1999_06
Patent number
US05908859

Reaction notes

Loading…