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

HRID 1080482Notes

Reaction equation

HRID 1080482 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](O)=[O:18])=[CH:12][CH:11]=1>>[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]([C:4]2[CH:5]=[CH:6][C:1]([S:7][CH3:8])=[CH:2][CH:3]=2)=[O:18])=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 7520ThioanisoleHCID 98372-(4-Fluorophenyl)acetic acid

Product 1

HCID 114709614-Fluorophenyl-1-[4-(methylthio)phenyl]ethanoneYield 63.2%

Conditions

Temperature
40 °C

Procedure

Thioanisole (10.1 g, 81.5 mmol) and 4-fluorophenylacetic acid (10.0 g, 65 mmol) were combined in a round bottom 3-neck flask. Polyphosphoric acid (PPA) (160 g), warmed to 60° C., was added and the mixture was heated to 120°-125° C. under nitrogen with vigorous stirring for 20 minutes. Upon cooling to 40° C., ice water and ice were added with vigorous stirring. The temperature was kept below 85° C. during the quench and dissolution of PPA. After cooling to 25° C., the white solids were filtered off, washed with two portions of water and dried. Recrystallization from ethyl acetate-hexane afforded the ketone (10.7 g, 63%): mp 139°-140° C. Elemental analysis Calc'd. for C15H13FOS: C, 69.21, H, 5.03, S, 12.32. Found: C, 68.74, H, 5.09, S, 12.15.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated to 120°-125° C. under nitrogen
  3. customwas kept below 85° C.
  4. customquench
  5. dissolutiondissolution of PPA
  6. temperatureAfter cooling to 25° C.
  7. filtrationthe white solids were filtered off
  8. washwashed with two portions of water
  9. customdried
  10. customRecrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-5127e23d3df64a50bd02484980be2f11
Source dataset
uspto-grants-1996_12
Patent number
US05580985

Reaction notes

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