N-bromobutanimide → HCID 19940138, Verbindung

HRID 1493523Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1493523
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[NH:7][C:8]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)=[CH:9][CH:10]=1.[Br:16]N1C(=O)CCC1=O>O1CCCC1>[Br:16][C:9]1[CH:10]=[C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)[NH:7][C:8]=1[C:11]1[S:12][CH:13]=[CH:14][CH:15]=1

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 41751102,5-Di(thiophen-2-yl)-1H-pyrrole

Produkt 1

HCID 19940138HCID 19940138, VerbindungAusbeute 46,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2,5-dithienylpyrrole (130 mg, 0.56 mmol) in 2.5 mL of anhydrous tetrahydrofuran cooled to -78° C. was added N-bromosuccinimide (99.68 mg, 0.56 mmol). After addition was complete the cooling bath was removed and the reaction mixture was allowed to stand in a -20° C. freezer for 4 hours, during which the solution became a brown color. The reaction mixture was concentrated under reduced pressure, carbon tetrachloride was added to precipitate the succinimide, and this mixture was filtered. The filter cake was washed with additional chloroform, the combined filtrates were concentrated, and the resulting oil was chromatographed on silica gel (50 g). Elution with hexane-ethyl acetate, 4:1, furnished 81 mg (46%) of 3-bromo-2,5-dithienylpyrrole.

Aufarbeitung

  1. additionAfter addition
  2. customwas removed
  3. concentrationThe reaction mixture was concentrated under reduced pressure, carbon tetrachloride
  4. additionwas added
  5. customto precipitate the succinimide
  6. filtrationthis mixture was filtered
  7. washThe filter cake was washed with additional chloroform
  8. concentrationthe combined filtrates were concentrated
  9. customthe resulting oil was chromatographed on silica gel (50 g)
  10. washElution with hexane-ethyl acetate, 4:1

Quellen und Nachweise

ORD-Eintrag
ord-a74c78877163428880338a2ee93e1ad8
Quelldatensatz
uspto-grants-1991_06
Patentnummer
US05021586

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