2,3-Dibromothiophene → HCID 66857536, Verbindung

HRID 252260

Reaktionsgleichung

Reaktionsgleichung von HRID 252260
Br[C:2]1[S:3][CH:4]=[CH:5][C:6]=1[Br:7].[Li]CCCC.[CH3:13][O:14][CH2:15][CH2:16]OS(C1C=CC(C)=CC=1)(=O)=O>C1COCC1>[Br:7][C:6]1[CH:5]=[CH:4][S:3][C:2]=1[CH2:16][CH2:15][O:14][CH3:13]

Komponenten

5

Edukt 3

HCID 765902,3-DibromothiopheneHCID 86977Ethanol, 2-methoxy-, 1-(4-methylbenzenesulfonate)HCID 178418339Butyllithium

Produkt 1

HCID 66857536HCID 66857536, VerbindungAusbeute 16,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-75 °C

Versuchsvorschrift

To a solution of 2,3-dibromothiophene (12.6 g, 50 mmol) in THF abs. (125 mL) was added at −75° C. n-BuLi (1.6M/hexane, 31 mL) over 30 minutes. The reaction mixture was further stirred at −75° C. for 30 minutes, and p-toluenesulfonic acid-2-methoxyethylester (11.8 g, 50 mmol) was added dropwise over 1 h. The mixture stirred for 2 h without cooling, quenched with brine, and extracted with ether. The organics were washed, dried, and concentrated. The residue was chromatographed on silica gel using heptane/ethyl acetate as eluent to obtain 3-bromo-2-(2-methoxy-ethyl)-thiophene (1.8 g) as a colorless liquid. MS (EI): 221.1 (M)

Aufarbeitung

  1. stirringThe mixture stirred for 2 h
  2. temperaturewithout cooling
  3. customquenched with brine
  4. extractionextracted with ether
  5. washThe organics were washed
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-dcfd055774cc4157887389e16aa1ef46
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868030B2

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