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Sulfur Dioxide → Lithium 4-methyl-3-thiophenesulfinate

HRID 1248378
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1248378
Br[C:2]1[C:6]([CH3:7])=[CH:5][S:4][CH:3]=1.C([Li:12])CCC.[S:13](=[O:15])=[O:14]>C(OCC)C.CCCCCC>[CH3:7][C:6]1[C:2]([S:13]([O-:15])=[O:14])=[CH:3][S:4][CH:5]=1.[Li+:12]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 1119Sulfur DioxideHCID 27349353-Bromo-4-methylthiopheneHCID 178418339Butyllithium

Produkt 1

HCID 23669555Lithium 4-methyl-3-thiophenesulfinate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

To 30 g of 3-bromo-4-methylthiophene in 150 ml of anhydrous ethyl ether under nitrogen at -70° to -75° C. was added, cautiously, during 30 minutes 111 ml of 1.6M butyl lithium in hexane. The mixture was stirred for an additional thirty minutes and then 30 ml of liquified sulfur dioxide was added at such a rate that the temperature of the reaction mixture was maintained below -70° C. Upon completion of the addition, the mixture was stirred for an additional 90 minutes at -75° C. and then allowed to stand overnight at room temperature. The resulting precipitate was filtered and washed with ethyl ether, dried in air and in vacuo under nitrogen to yield 30 g of the desired salt, m.p. >250° C.

Aufarbeitung

  1. temperaturewas maintained below -70° C
  2. additionUpon completion of the addition
  3. stirringthe mixture was stirred for an additional 90 minutes at -75° C.
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with ethyl ether
  6. customdried in air and in vacuo under nitrogen

Quellen und Nachweise

ORD-Eintrag
ord-9c83418814a64a63b686491b5acf7391
Quelldatensatz
uspto-grants-1985_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04523943

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