Hydrochloric Acid → 1-(4-Fluorophenyl)-2-(4-methylthiophenyl)ethanone

HRID 1090869Notes

Reaction equation

HRID 1090869 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][S:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14](Cl)=[O:15])=[CH:9][CH:8]=1.Cl.[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:14](=[O:15])[CH2:13][C:10]2[CH:11]=[CH:12][C:7]([S:6][CH3:5])=[CH:8][CH:9]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 10008Fluorobenzene2×HCID 6451240Aluminum(III) ChlorideHCID 150201874-(Methylthio)phenylacetyl chloride

Product 1

HCID 112539741-(4-Fluorophenyl)-2-(4-methylthiophenyl)ethanoneYield 40%

Conditions

Temperature
20 °C

Procedure

Thereafter 174 g (1.3 moles) of anhydrous aluminum chloride was suspended in 600 ml of fluorobenzene. To the suspension was added dropwise a solution of 175 g of 4-methylthiophenylacetyl chloride obtained in the same manner as above in 120 ml of fluorobenzene at a temperature of 0° to 3° C. The resulting mixture was stirred at 20° C. for 3.5 hours. Then the reaction mixture was gradually poured into a mixture of ice water and hydrochloric acid, followed by extraction with dichloromethane. The dichloromethane layer was washed sequentially with a 5% aqueous solution of sodium bicarbonate and a saturated saline solution and dried over magnesium sulfate. The dichloromethane was distilled off and the resulting crystals were dissolved in 300 ml of a 2:1 mixture of ethyl acetate and isopropyl ether with heating. Ten grams of activated carbon was added and the solution was filtered. The separated crystals were collected by filtration, giving 92 g (40%) of 1-(4-fluorophenyl)-2-(4-methylthiophenyl)ethanone as pale yellow solids.

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. washThe dichloromethane layer was washed sequentially with a 5% aqueous solution of sodium bicarbonate
  3. dry with materiala saturated saline solution and dried over magnesium sulfate
  4. distillationThe dichloromethane was distilled off
  5. dissolutionthe resulting crystals were dissolved in 300 ml of a 2:1 mixture of ethyl acetate and isopropyl ether
  6. temperaturewith heating
  7. additionTen grams of activated carbon was added
  8. filtrationthe solution was filtered
  9. filtrationThe separated crystals were collected by filtration

Sources & evidence

ORD record
ord-ffa921b6fcd54115844e1928f9f91ec9
Source dataset
uspto-grants-1992_01
Patent number
US05082974

Reaction notes

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