4-Bromo-2,6-xylidine → N-(4-Bromo-2,6-dimethylphenyl)(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl) dimethylsilanamine

HRID 1037716

Reaktionsgleichung

Reaktionsgleichung von HRID 1037716
[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:5]([NH2:6])=[C:4]([CH3:10])[CH:3]=1.[Li]CCCC.Cl[Si:17]([CH:20]1[C:24]2[S:25][CH:26]=[CH:27][C:23]=2[C:22]([CH3:28])=[C:21]1[CH3:29])([CH3:19])[CH3:18]>C1COCC1>[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:5]([NH:6][Si:17]([CH:20]2[C:24]3[S:25][CH:26]=[CH:27][C:23]=3[C:22]([CH3:28])=[C:21]2[CH3:29])([CH3:18])[CH3:19])=[C:4]([CH3:10])[CH:3]=1

Komponenten

5

Edukt 3

HCID 905494-Bromo-2,6-xylidineHCID 58526148Chloro(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilaneHCID 178418339Butyllithium

Produkt 1

HCID 58526147N-(4-Bromo-2,6-dimethylphenyl)(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl) dimethylsilanamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Under an argon atmosphere, to a solution of 12.4 g (61.9 mmol) of 4-bromo-2,6-dimethylaniline in 300 ml of THF, 16.5 ml of 2.5 M (41.2 mmol) nBuLi in hexanes was added at −80° C. This mixture was warmed for ca. 2 hour to ambient temperature. Then, the resulting solution was added dropwise over ca. 1 hour, while vigorously stirring, to a solution of 10.0 g (41.2 mmol) of chloro(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilane in 50 ml of THF. The resulting mixture was stirred overnight at ambient temperature, and then, evaporated to dryness. To the residue, 150 ml of toluene was added. This mixture was filtered through a glass frit (G4). The filtrate was evaporated to dryness. Fractional distillation gave a yellow liquid, bp 154-156° C./0.05 mm Hg. The product crystallizes slowly at ambient temperature. Yield 8.36 g (50%).

Aufarbeitung

  1. temperatureThis mixture was warmed for ca. 2 hour to ambient temperature
  2. additionThen, the resulting solution was added dropwise over ca. 1 hour
  3. customevaporated to dryness
  4. additionTo the residue, 150 ml of toluene was added
  5. filtrationThis mixture was filtered through a glass frit (G4)
  6. customThe filtrate was evaporated to dryness
  7. distillationFractional distillation
  8. customgave a yellow liquid, bp 154-156° C./0.05 mm Hg
  9. customThe product crystallizes slowly at ambient temperature

Quellen und Nachweise

ORD-Eintrag
ord-8eec73bc0fbd495aaab6d09a4b9ce60e
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546595B2

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