Water → HCID 18388321, Verbindung

HRID 1108331Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1108331
[CH:1]([S:4][C:5]1[S:9][C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:7]2[CH2:15][CH2:16][CH2:17][C:18](=[O:19])[C:6]=12)([CH3:3])[CH3:2].[Br:20]Br.O>CO>[Br:20][CH:17]1[CH2:16][CH2:15][C:7]2=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[S:9][C:5]([S:4][CH:1]([CH3:2])[CH3:3])=[C:6]2[C:18]1=[O:19]

Komponenten

5

Edukt 3

HCID 962WaterHCID 24408BromineHCID 2820027ethyl 4-oxo-3-propan-2-ylsulfanyl-6,7-dihydro-5H-2-benzothiophene-1-carboxylate

Produkt 1

HCID 18388321HCID 18388321, VerbindungAusbeute 83,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

Ethyl 4,5,6,7-tetrahydro-3-isopropylthio-4-oxobenzo[c]thiophene-1-carboxylate (2.50 g) was dissolved in methanol (80 ml); a solution of bromine (1.34 g) in methanol (8.6 ml) was added dropwise at room temperature. After the reaction mixture was stirred at room temperature for 2 hours, it was poured over water and extracted with ethyl acetate. The organic layer was washed with an aqueous solution of sodium thiosulfate, a saturated aqueous solution of sodium hydrogen carbonate and water in that order, and dried (MgSO4), after which the solvent was distilled off. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:5, v/v) to yield ethyl 5-bromo-4,5,6,7-tetrahydro-3-isopropylthio-4-oxobenzo[c]thiophene-1-carboxylate (2.65 g, 83.9%), which was then recrystallized from ethyl acetate-hexane. Colorless prisms. Melting point 107-108° C.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous solution of sodium thiosulfate
  3. dry with materiala saturated aqueous solution of sodium hydrogen carbonate and water in that order, and dried (MgSO4)
  4. distillationafter which the solvent was distilled off
  5. washeluted with ethyl acetate-hexane (1:5

Quellen und Nachweise

ORD-Eintrag
ord-b30a0a7415b84d8b8a999605f4e7fd7f
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06066658

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