Bismuth-oxygen → 1-(4-Methylthiophenyl)-2-(4-fluorophenyl)-ethane-1,2-dione

HRID 2231097Notes

Reaction equation

HRID 2231097 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:19])[CH:9]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)[OH:10])=[CH:4][CH:3]=1.[Bi]=O>C(O)(=O)C>[CH3:18][S:17][C:14]1[CH:15]=[CH:16][C:11]([C:9](=[O:10])[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[O:19])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 6327914Bismuth-oxygenHCID 541534701-(4-Fluorophenyl)-2-hydroxy-2-[4-(methylsulfanyl)phenyl]ethan-1-one

Product 1

HCID 221820391-(4-Methylthiophenyl)-2-(4-fluorophenyl)-ethane-1,2-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ketone from step 2 (1.25 g, 4.5 mmol) and bismuth oxide (Bi2O3) (2.7 g, 1.2 equiv.) in acetic acid (20 ml) was warmed to 80° C. for 30 minutes. After cooling, the mixture was filtered through Celite® filter agent and the filtrate was concentrated. The residue was dissolved in hot methanol and filtered. The solvent was concentrated under a nitrogen stream, placed in the refrigerator and the precipitate formed was filtered to give 1 g (83%) of titled dione: m.p. 96-970° C. Anal. Calc'd. for C15H11FO2S (M.W. 274.31): C, 65.68; H, 4.04; S, 11.69. Found: C, 65.42; H, 3.85; S, 11.42.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered through Celite®
  3. filtrationfilter agent
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe residue was dissolved in hot methanol
  6. filtrationfiltered
  7. concentrationThe solvent was concentrated under a nitrogen stream
  8. customthe precipitate formed
  9. filtrationwas filtered
  10. customto give 1 g (83%) of titled dione

Sources & evidence

ORD record
ord-64afef6352454c27adcc35f6fac80227
Source dataset
uspto-grants-2002_07
Patent number
US06426360B1

Reaction notes

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