HCID 11337288, compound → HCID 11280269, compound

HRID 1359533Notes

Reaction equation

HRID 1359533 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:13][S:12][C:11]=2[C:21]([O:23][CH3:24])=[O:22])[CH:5]=[CH:6][C:7]=1[S:8][CH3:9].O.O.O.O.O.O.C(O[O-])(=O)C1C(=CC=CC=1)C([O-])=[O:35].[Mg+2]>ClCCl.CO>[F:1][C:2]1[CH:3]=[C:4]([C:10]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:13][S:12][C:11]=2[C:21]([O:23][CH3:24])=[O:22])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:9])=[O:35]

Participants

5

Reactant 2

HCID 11337288HCID 11337288, compoundHCID 21894687Magnesium 2-(dioxidan-2-ide-1-carbonyl)benzoate--water (1/1/6)2×

Product 1

HCID 11280269HCID 11280269, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

The methyl 3-[3-fluoro-4-(methylthio)phenyl]-4-phenyl-2-thiophenecarboxylate (5.00 g, 13.9 mmol) was dissolved in dichloromethane (100 mL) and methanol (30 mL). Magnesium monoperoxyphathalate hexahydrate (MMPP)(3.78 g of 80%, 7.6 mmol) was added in five equal portions at one minute intervals. The resulting heterogeneous solution was stirred for 1 hour. Additional MMPP (600 mg, 1.6 mmol) was added and the solution stirred for 15 min. The reaction was complete and solution extracted with saturated sodium bicarbonate (2×100 mL). The organic layer was dried over sodium sulfate and solvent removed at reduced pressure. Methyl 3-[3-fluoro-4-(methylsulfinyl)phenyl]-4-phenyl-2-thiophenecarboxylate was isolated by crystallization from dichloromethane and hexanes. (81% yield): Mp 164.0-164.1° C. 1H NMR (CDCl3/300 MHz) 7.75 (t, 1H, J=7.7 Hz), 7.53 (s, 1H), 7.15-7.26 (m, 3H), 6.94-7.40 (m, 3H), 3.90 (s, 3H), 2.85 (s, 3H). ESHRMS m/z 375.0536 (calcd for M+H, 375.0525).

Workup

  1. stirringthe solution stirred for 15 min
  2. extractionsolution extracted with saturated sodium bicarbonate (2×100 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate and solvent
  4. customremoved at reduced pressure

Sources & evidence

ORD record
ord-798fab41eda242eab9b7432836048359
Source dataset
uspto-grants-2003_07
Patent number
US06600052B1

Reaction notes

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