Perchloric Acid → Methyl 5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]thiophene-2-acetate

HRID 1899076Notes

Reaction equation

HRID 1899076 reaction equation
C([C:4]1[S:8][C:7]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[C:6]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[CH:5]=1)(=O)C.[OH2:26].O.O.[N+]([O-])([O-])=O.[Tl+3].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.Cl(O)(=O)(=O)=O.[O:47]1[CH2:52]CO[CH2:49][CH2:48]1>CO>[F:15][C:12]1[CH:11]=[CH:10][C:9]([C:7]2[S:8][C:4]([CH2:49][C:48]([O:47][CH3:52])=[O:26])=[CH:5][C:6]=2[C:16]2[CH:17]=[CH:18][C:19]([S:22]([CH3:25])(=[O:23])=[O:24])=[CH:20][CH:21]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 24247Perchloric AcidHCID 312751,4-DioxaneHCID 106431405-Acetyl-2-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]thiopheneHCID 11270721Nitric acid,thallium(3+) salt, trihydrate (9CI)

Product 1

HCID 11795515Methyl 5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]thiophene-2-acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-acetyl-2-(4-fluorophenyl)-3-[4-(methylsulfonyl)phenyl]thiophene (1 g), thallium(III) nitrate trihydrate (1.4 g) and perchloric acid (70%; 3 ml) in methanol (15 ml) and dioxane (7 ml) was stirred at ambient temperature for 7 hours. The insoluble material was filtered. The filtrate was diluted with water and extracted with chloroform. The extract was dried over magnesium sulfate and concentrated to give an oil of methyl 5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]thiophene-2-acetate (1.2 g).

Workup

  1. filtrationThe insoluble material was filtered
  2. additionThe filtrate was diluted with water
  3. extractionextracted with chloroform
  4. dry with materialThe extract was dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-37685fd9099041ecabedfd739fc59f56
Source dataset
uspto-grants-1996_11
Patent number
US05571810

Reaction notes

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