N-bromobutanimide → HCID 70818321, Verbindung

HRID 590990

Reaktionsgleichung

Reaktionsgleichung von HRID 590990
[Br:1]N1C(=O)CCC1=O.[C:9]1([C:15]2[S:19][CH:18]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[CH:16]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CN(C)C=O.O1CCCC1.O>[Br:1][C:18]1[S:19][C:15]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:16][C:17]=1[C:20]([O:22][CH3:23])=[O:21]

Komponenten

6

Edukt 2

HCID 67184N-bromobutanimide2×HCID 819151Methyl 5-phenylthiophene-3-carboxylate

Produkt 1

HCID 70818321HCID 70818321, VerbindungAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-Bromosuccinimide (360 mg, 2.02 mmol) was added to a solution of methyl 5-phenylthiophene-3-carboxylate (11b) (440 mg, 2.02 mmol) in a mixture of N,N-dimethylformamide (4 mL) and tetrahydrofuran (4 mL). The reaction mixture was stirred at room temperature for 1 hour. N-Bromosuccinimide (72 mg, 0.40 mmol) was added and the stirring was maintained for 1 hour. The mixture was poured in water (10 mL) and extracted with dichloromethane (2×15 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10) to provide the desired product (11c) (390 mg, 1.3 mmol, 65%).

Aufarbeitung

  1. temperaturethe stirring was maintained for 1 hour
  2. extractionextracted with dichloromethane (2×15 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10)

Quellen und Nachweise

ORD-Eintrag
ord-90b33ae717a1431eadc6e7c8d26b1c8a
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238026B2

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