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4-Vinylpyridine → 4,4'-(9,9-Bis-n-decyl-2,7-fluorenediyldi-2,1-ethenediyl)bis-pyridine

HRID 342906
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 342906
Br[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8](Br)=[CH:9][CH:10]=3)[C:5]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:4]=2[CH:3]=1.[C:36]1(C)[CH:41]=CC=C[C:37]=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[CH:58]([C:60]1[CH:65]=[CH:64][N:63]=[CH:62][CH:61]=1)=[CH2:59].C([N:68]([CH2:71][CH3:72])[CH2:69][CH3:70])C>[Pd]>[CH2:26]([C:5]1([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:6]2[CH:7]=[C:8]([CH:59]=[CH:58][C:60]3[CH:65]=[CH:64][N:63]=[CH:62][CH:61]=3)[CH:9]=[CH:10][C:11]=2[C:12]2[C:4]1=[CH:3][C:2]([CH:37]=[CH:36][C:41]1[CH:70]=[CH:69][N:68]=[CH:71][CH:72]=1)=[CH:14][CH:13]=2)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 75024-VinylpyridineHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 36612112,7-Dibromo-9,9-didecylfluorene

Produkt 1

HCID 675756704,4'-(9,9-Bis-n-decyl-2,7-fluorenediyldi-2,1-ethenediyl)bis-pyridineAusbeute 71,48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938
Palladium
Katalysator

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

2,7-Dibromo-9,9-di-n-decyl-9H-fluorene (10.0 g, 16.5 mmol), tri-o-tolylphosphine (2.01 g, 6.6 mmol), degassed triethylamine (40 ml) and 4-vinylpyridine (5.35 ml, 49.62 mmol) was added to a single-necked round bottom flask under to nitrogen equipped with a magnetic stir bar and a reflux condenser. The palladium catalyst (0.19 g, 0.83 mmol) was added and the solution heated at 95° C. for 18 hours. The reaction mixture was cooled to room temperature and the solvent removed under reduced pressure. The residue was dissolved in methylene chloride, and the organic layer washed three times with equal volumes of water, dried over anhydrous MgSO4, filtered and concentrated. The product was purified by column chromotography on alumina using 30/70 ethyl acetate/hexane to yield the product as a yellow oil in 71.48% yield.Mass Spec. m/z 652 (M+), 511 (M--C10H21). Elemental Analysis: Calculated for C47H60N2 : C, 86.45, H, 9.26, N, 4.29. Found: C, 86.50, H, 8.84, N, 3.78.

Aufarbeitung

  1. additionwas added to a single-necked round bottom flask under to nitrogen
  2. customequipped with a magnetic stir bar and a reflux condenser
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customthe solvent removed under reduced pressure
  5. dissolutionThe residue was dissolved in methylene chloride
  6. washthe organic layer washed three times with equal volumes of water
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe product was purified by column chromotography on alumina using 30/70 ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-ed72695deaa241cba0ef112315c050f6
Quelldatensatz
uspto-grants-1999_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05859251

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