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Water → 4-[3,5-Difluoro-4-(methylsulfonyl)phenyl]-3-phenylfuran-2(5h)-one

HRID 1838500
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1838500
[F:1][C:2]1[CH:3]=[C:4]([C:11]2[CH2:15][O:14][C:13](=[O:16])[C:12]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:5]=[C:6]([F:10])[C:7]=1[S:8][CH3:9].[OH2:23].[OH2:24].O.O.O.O.C(OO)(=O)C1C(=CC=CC=1)C(O)=O.O.O.O.O.O.O.O.C(O[O-])(=O)C1C(=CC=CC=1)C([O-])=O.[Mg+2]>ClCCl.CO>[F:1][C:2]1[CH:3]=[C:4]([C:11]2[CH2:15][O:14][C:13](=[O:16])[C:12]=2[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:5]=[C:6]([F:10])[C:7]=1[S:8]([CH3:9])(=[O:24])=[O:23]
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Komponenten

7

Edukt 4

HCID 962Water2×HCID 21894687Magnesium 2-(dioxidan-2-ide-1-carbonyl)benzoate--water (1/1/6)HCID 227466594-[3,5-difluoro-4-(methylthio)-phenyl]-3-phenylfuran-2(5H)-oneHCID 131724279Monoperoxyphthalate hexahydrate

Produkt 1

HCID 99682544-[3,5-Difluoro-4-(methylsulfonyl)phenyl]-3-phenylfuran-2(5h)-one
Ausbeute 70,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Unpurified 4-[3,5-difluoro-4-(methylthio)-phenyl]-3-phenylfuran-2(5H)-one (8.9 g, 27 mmol) and magnesum monoperoxyphthalate hexahydrate (17.2 g, 27 mmol) were combined in a mixture of dichloromethane (200 mL) and methanol (60 mL), and stirred overnight at room temperature. The slurry was poured into water, and extracted with dichloromethane (1×200 mL, 2×50 mL). The combined extracts were washed with water and dilute sodium bicarbonate, and the aqueous sodium bicarbonate wash extracted with dichloromethane (50 mL). The combined extracts were dried with magnesium sulfate, filtered and concentrated. The residue was treated again with magnesium monoperoxyphthalate hexahydrate (8.5 g., 25 mmol), in a mixture of dichloromethane (120 mL) and methanol (30 mL), stirring overnight at room temperature. The reaction mixture was poured into water, and extracted with dichloromethane (2×200 mL). The combined extracts were washed with dilute ammonium chloride (100 mL), and dilute sodium chloride (100 mL), dried with magnesium sulfate, and concentrated to give 6.7 g yellow solids. The crude product was dissolved in dichloromethane (20 mL), and crystallized by adding a mixture of 40% ethyl acetate/60% hexanes (15 mL). The product was filtered, and the filtrate purified by silica gel chromatography using 40% ethyl acetate/60% hexanes to give a total of 5.3 g yellow solids (56%). The 4-[3,5-difluoro-4-(methylsulfonyl)phenyl]-3-phenylfuran-2(5H)-one was recrystallized from ethyl acetate to give white solids. MP 203.5-203.8° C. 1H NMR (CDCl3/400 MHz) 7.35-7.44 (m, 5H), 6.97 (d, 2H, J=9.0), 5.11 (s, 2H), 3.29 (s, 3H). ESHRMS m/z 351.0536 (M+H+, Calcd 351.0502). Anal. Calcd for C17H12F2O4S: C, 58.28; H, 3.45; Found: C, 57.69; H, 3.72.

Aufarbeitung

  1. extractionextracted with dichloromethane (1×200 mL, 2×50 mL)
  2. washThe combined extracts were washed with water and dilute sodium bicarbonate
  3. washthe aqueous sodium bicarbonate wash
  4. extractionextracted with dichloromethane (50 mL)
  5. dry with materialThe combined extracts were dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. stirringstirring overnight at room temperature
  9. extractionextracted with dichloromethane (2×200 mL)
  10. washThe combined extracts were washed with dilute ammonium chloride (100 mL), and dilute sodium chloride (100 mL)
  11. dry with materialdried with magnesium sulfate
  12. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-258d77ce4e7e4ec6abc690b522fe5e6d
Quelldatensatz
uspto-grants-2004_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06673818B2

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