Water → 4-(3-Allyloxy-5-bromo-benzenesulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester

HRID 723040Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 723040
C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:7](Br)[CH:8]=[CH2:9].[CH3:11][O:12][C:13]([C:15]1[S:16][C:17]([S:31][CH3:32])=[C:18]([S:20]([C:23]2[CH:28]=[C:27]([OH:29])[CH:26]=[C:25]([Br:30])[CH:24]=2)(=[O:22])=[O:21])[CH:19]=1)=[O:14].O>CN(C=O)C.CCOC(C)=O>[CH3:11][O:12][C:13]([C:15]1[S:16][C:17]([S:31][CH3:32])=[C:18]([S:20]([C:23]2[CH:24]=[C:25]([Br:30])[CH:26]=[C:27]([O:29][CH2:9][CH:8]=[CH2:7])[CH:28]=2)(=[O:21])=[O:22])[CH:19]=1)=[O:14]

Komponenten

7

Edukt 4

HCID 962WaterHCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 210571774-(3-Bromo-5-hydroxy-benzenesulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester

Produkt 1

HCID 695867464-(3-Allyloxy-5-bromo-benzenesulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Cesium carbonate (33 mg, 0.1 mmol) and allylbromide (30 μL, 0.35 mmol) were added to a solution of 4-(3-bromo-5-hydroxy-benzenesulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester ((Example 12: step d) 30 mg, 0.71 mmol) dissolved in dry DMF (3 mL). After stirring for 16 h at rt, the solution was poured into a mixture of water (20 mL) and EtOAc (30 mL). The layers were separated and the organic layer was extracted with water (5×5 mL), brine (20 mL), and was dried over sodium sulfate. The solvent was removed in vacuo to yield the title compound, which was used without further purification.

Aufarbeitung

  1. customThe layers were separated
  2. extractionthe organic layer was extracted with water (5×5 mL), brine (20 mL)
  3. dry with materialwas dried over sodium sulfate
  4. customThe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-55f8604ddd0d4661b9c873930368db13
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138530B2

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