Fluorobenzene → 1-(4-Fluorophenyl)-2-(4-methylthiophenyl)ethanone

HRID 433918Notes

Reaction equation

HRID 433918 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.[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[F:17][C:18]1[CH:23]=[CH:22][C:21]([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:20][CH:19]=1

Participants

4

Reactant 3

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

Product 1

HCID 112539741-(4-Fluorophenyl)-2-(4-methylthiophenyl)ethanoneYield 55%

Conditions

Temperature
50 °C

Procedure

A mixture of fluorobenzene (181 mL) and aluminum chloride (18.5 g, 139 mmol) was treated with a solution of 4-methylthiophenyl acetic chloride (21.9 g, 120 mmol) in 37 mL of fluorobenzene. When the addition was completed, the mixture was stirred at 50° C. for 3 h. The reaction mixture was then poured into ice water and stirred for 1 h. It was extracted with chloroform and washed with 5% aqueous sodium bicarbonate solution and with brine. The organic layer was separated and dried over anhydrous sodium sulfate. The drying agent was filtered and the filtrate concentrated in vacuum to give 15.6 g (55%) of the desired compound as a yellow solid.

Workup

  1. additionWhen the addition
  2. stirringstirred for 1 h
  3. extractionIt was extracted with chloroform
  4. washwashed with 5% aqueous sodium bicarbonate solution and with brine
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe drying agent was filtered
  8. concentrationthe filtrate concentrated in vacuum

Sources & evidence

ORD record
ord-ae36f6171817439ba1be52ba32563308
Source dataset
uspto-grants-2003_12
Patent number
US06670365B1

Reaction notes

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