Chloride → 1-(4-Cyclopropylsulfanylphenyl)ethanone

HRID 1038565Notes

Reaction equation

HRID 1038565 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl-].[CH:6]1([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7]1.Cl>ClCCl>[CH:6]1([S:9][C:10]2[CH:15]=[CH:14][C:13]([C:1](=[O:3])[CH3:2])=[CH:12][CH:11]=2)[CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 312ChlorideHCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 123348Benzene, (cyclopropylthio)-

Product 1

HCID 580226851-(4-Cyclopropylsulfanylphenyl)ethanoneYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To dichloromethane (6.7 mL), acetyl chloride (189 μL, 2.66 mmol) and alminium chloride (267 mg, 2.0 mmol) were added sequentially at 0° C., and the mixture was stirred at 0° C. for 10 minutes. Then, a solution of cyclopropyl(phenyl)sulfane (200 mg, 1.33 mmol) in dichloromethane (890 μL) was added, and stirred at 0° C. for 0.5 hours. The reaction solution was added 5% aqueous solution of hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate), and 1-(4-(cyclopropylthio)phenyl)ethanone (181 mg (yield 71%)) was obtained as a colorless oil.

Workup

  1. stirringstirred at 0° C. for 0.5 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-97cb3e90dd264c0cb3be9a915bacacc9
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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