Sodium methanethiolate → 6-Methylsulfanylbenzo[b]thiophene

HRID 1986208Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1986208
Br[C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[CH:10]=1.[CH3:11][S-:12].[Na+]>CN(C=O)C>[CH3:11][S:12][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[CH:10]=1

Komponenten

4

Edukt 2

HCID 4378561Sodium methanethiolateHCID 127444006-Bromo-benzo[b]thiophene

Produkt 1

HCID 198037266-Methylsulfanylbenzo[b]thiopheneAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 6-bromobenzo[b]thiophene (2.0 g, 9.4 mmol) and sodium thiomethoxide (1.30 g, 18.8 mmol) in DMF (15 mL) is stirred at 90° C. under nitrogen for 6 hours. The reaction is cooled to room temperature, extracted with ethyl acetate and saturated aqueous sodium chloride, washed with 2 N aqueous NaOH solution, saturated aqueous sodium chloride, dried over Na2SO4, filtered, and evaporated. The residue is purified by chromatography on silica gel, eluting with ethyl acetate:hexanes 3:7, to give the title product as a red liquid (1.41 g) which is used for next reaction without further purification.

Aufarbeitung

  1. temperatureThe reaction is cooled to room temperature
  2. extractionextracted with ethyl acetate and saturated aqueous sodium chloride
  3. washwashed with 2 N aqueous NaOH solution, saturated aqueous sodium chloride
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by chromatography on silica gel
  8. washeluting with ethyl acetate:hexanes 3:7

Quellen und Nachweise

ORD-Eintrag
ord-83d3ffda27a649bfb8c37423a07d4f9b
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07547691B2

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