Water → 4-Fluorophenyl-1-[4-(methylthio)phenyl]ethanone

HRID 1378578Notes

Reaction equation

HRID 1378578 reaction equation
[C:1]1([S:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17](Cl)=[O:18])=[CH:12][CH:11]=1.[Cl-].[Al+3].[Cl-].[Cl-].O>C(=S)=S>[CH3:8][S:7][C:1]1[CH:6]=[CH:5][C:4]([C:17](=[O:18])[CH2:16][C:13]2[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7520ThioanisoleHCID 37449884-Fluorophenylacetyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 114709614-Fluorophenyl-1-[4-(methylthio)phenyl]ethanoneYield 48%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a stirred solution of thioanisole (380 mL, 3.2 mol) and 4-fluorophenylacetyl chloride (300 g, 1.6 mol) in carbon disulfide (1.2 L), cooled to 5° C., was added anhydrous aluminum chloride portionwise at such a rate that the internal temperature did not rise above 15° C. The reaction was stirred at room temperature for 16 hours. The solution was cautiously poured into 2 L of ice and water. The aqueous solution was extracted with methylene chloride (6×150 mL), the combined extracts were dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was dissolved in 800 mL of ether and cooled to 0° C. whereupon crystals of pure product formed which were isolated by filtration on a Buchner funnel and air dried to provide the ketone (199.6 g, 48%): mp 135°-138° C. 1H NMR (CDCl3 /TMS) 300 MHz 8.00 (d, J=8.7 Hz, 2H), 7.40-7.30 (m, 4H), 7.13-7.03 (m, 2H), 4.34 (s, 2H), 2.56 (s, 3H). Mass spectrum M+ =260.

Workup

  1. customdid not rise above 15° C
  2. extractionThe aqueous solution was extracted with methylene chloride (6×150 mL)
  3. dry with materialthe combined extracts were dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in 800 mL of ether
  7. temperaturecooled to 0° C. whereupon crystals of pure product
  8. customformed which
  9. customwere isolated by filtration on a Buchner funnel and air
  10. customdried

Sources & evidence

ORD record
ord-3db37df4379241de8f505592abfe6f9f
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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