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

HRID 2215993Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2215993
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-f93ea7b5844b4a479d6834be34fc1898
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109354B2

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