Fluorene → HCID 69977936, Verbindung

HRID 1075375

Reaktionsgleichung

Reaktionsgleichung von HRID 1075375
C([Li])CCC.[CH:6]1[C:18]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=2[CH:9]=[CH:8][CH:7]=1.Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].Br[CH2:27][CH2:28][CH2:29][CH2:30][C:31]([CH3:35])([CH3:34])[C:32]#[N:33]>CCCCCC.O1CCCC1.O>[CH2:20]([C:17]1([CH2:27][CH2:28][CH2:29][CH2:30][C:31]([C:32]#[N:33])([CH3:35])[CH3:34])[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:18]1=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Komponenten

8

Edukt 4

HCID 6853FluoreneHCID 81011-BromohexaneHCID 46382156-Bromo-2,2-dimethylhexanenitrileHCID 178418339Butyllithium2×

Produkt 1

HCID 69977936HCID 69977936, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-7.5 °C

Versuchsvorschrift

2.4 g of butyllithium dissolved in 15 ml of hexane was slowly added during 5 minutes into 6.0 g of fluorene dissolved in 40 ml of anhydrous tetrahydrofuran at -50° C. under nitrogen protection. The mixture was stirred at -30 to 15° C. for 1 hour before it was cooled again to -40 ~-50° C. Then, 6.0 g of 1-bromohexane was added in 5 minutes. The mixture was subsequently stirred for 2 hours while the temperature was gradually increased to room temperature. The mixture was then cooled to -50° C., and 2.4 g of butyllithium dissolved in 15 ml of hexane was slowly added in 5 minutes under nitrogen protection. The mixture was stirred at -30 to 15° C. for 1 hour before it was cooled again to -40~-50° C. Then, 7.6 g of 6-bromo-2,2-dimethylhexanenitrile was added in 5 minutes. The mixture was subsequently stirred for 15 hours at room temperature, dispersed in water, and extracted with ether. The etheral solution was washed with water and brine, dried with magnesium sulfate, and evaporated. The residue was distilled to collect 12.4 g (92%) of light yellow liquid. MS (m/z): 373 (M+), 288, 249, 217, 191, 179, 165.

Aufarbeitung

  1. temperaturewas cooled again to -40 ~-50° C
  2. stirringThe mixture was subsequently stirred for 2 hours while the temperature
  3. temperaturewas gradually increased to room temperature
  4. temperatureThe mixture was then cooled to -50° C.
  5. additionwas slowly added in 5 minutes under nitrogen protection
  6. stirringThe mixture was stirred at -30 to 15° C. for 1 hour before it
  7. temperaturewas cooled again to -40~-50° C
  8. stirringThe mixture was subsequently stirred for 15 hours at room temperature
  9. extractionextracted with ether
  10. washThe etheral solution was washed with water and brine
  11. dry with materialdried with magnesium sulfate
  12. customevaporated
  13. distillationThe residue was distilled
  14. customto collect 12.4 g (92%) of light yellow liquid

Quellen und Nachweise

ORD-Eintrag
ord-ae0238323acb46f9af43d3973be69560
Quelldatensatz
uspto-grants-1999_05
Patentnummer
US05900327

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