Methyl iodide → 2-Methylbenzo(b)thiophene

HRID 234327

Reaktionsgleichung

Reaktionsgleichung von HRID 234327
[Li][C:2](C)(C)C.[S:6]1[CH:10]=[CH:9][C:8]2[CH:11]=[CH:12][CH:13]=[CH:14][C:7]1=2.C1COCC1.IC>CCOCC>[CH3:2][C:10]1[S:6][C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[CH:9]=1

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 7221Benzo(B)ThiopheneHCID 8028TetrahydrofuranHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 709522-Methylbenzo(b)thiophene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

t-BuLi (1.7M, 26 mmoles, 15 ml) was added to a stirred solution of benzo[b]thiophene (17 mmoles, 2.3 g) and THF (30 ml) at -50° C. The resulting bright yellow reaction mixture was warmed to -30° C., and iodomethane (26 mmoles, 1.6 ml) was added. After 10 min. at -30° C., the solution was warmed to ambient temperature and stirred an additional 30 min., then diluted with ether (100 ml) and washed with brine (2×100 ml). The organic phase was dried (MgSO4), filtered and concentrated to collect 2.48 g (98%) of 2-methylbenzo[b]thiophene as a light yellow solid.

Aufarbeitung

  1. temperaturethe solution was warmed to ambient temperature
  2. washwashed with brine (2×100 ml)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto collect 2.48 g (98%) of 2-methylbenzo[b]thiophene as a light yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-7907f0755a9a46be993b5afb3b109fd1
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05594021

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