Carbazole → 9-Allylcarbazole

HRID 1357878

Reaktionsgleichung

Reaktionsgleichung von HRID 1357878
[H-].[Na+].[CH:3]1[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH2:16](Br)[CH:17]=[CH2:18]>C1COCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:18]([N:14]1[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:7]2[C:15]1=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:17]=[CH2:16]

Komponenten

6

Edukt 3

HCID 6854CarbazoleHCID 7841Allyl bromideHCID 24758Sodium hydride

Produkt 1

HCID 30903939-AllylcarbazoleAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

Into a 500 mL round bottom flask fitted with a mechanical stirrer, addition funnel, reflux condenser and nitrogen inlet were placed 12 g of sodium hydride (60% dispersion in mineral oil) and 30 mL of THF. Carbazole (33.4 g, 0.2 mole) was dissolved in 200 mL THF and the pale yellow solution was added dropwise to the reaction mixture while stirring and maintaining the temperature at 35˜40° C. Thereafter, 36.2 g (0.3 mole) of allyl bromide was added drop wise to the reaction mixture and stirring continued for an additional 15 minutes. Tetra-n-butyl ammonium bromide (1.3 g) was added followed by stirring for 20 minutes, and then the temperature was raised to 65° C. and kept at that temperature overnight. The reaction mixture was cooled to room temperature and after filtration, the solvent was removed using a rotary evaporator. The resulting yellow solid was twice recrystallized from methanol to give 34 g (81% yield) of colorless crystalline 9-allyl carbazole m.p. 53-54° C.

Aufarbeitung

  1. customInto a 500 mL round bottom flask fitted with a mechanical stirrer, addition funnel
  2. temperaturereflux condenser and nitrogen inlet
  3. additionthe pale yellow solution was added dropwise to the reaction mixture
  4. temperaturemaintaining the temperature at 35˜40° C
  5. stirringstirring
  6. stirringby stirring for 20 minutes
  7. customkept at that temperature overnight
  8. temperatureThe reaction mixture was cooled to room temperature
  9. filtrationafter filtration
  10. customthe solvent was removed
  11. customa rotary evaporator
  12. customThe resulting yellow solid was twice recrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-034d7b822544432cb12ad4d0803dc37c
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06593388B2

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