1,2-Dimethoxyethane → 9,9-Diethyl-2,7-bis(4-octyloxybiphenyl-4'-yl)fluorene

HRID 915499

Reaktionsgleichung

Reaktionsgleichung von HRID 915499
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]([CH2:18][CH3:19])([CH2:16][CH3:17])[C:4]=2[CH:3]=1.[CH2:20]([O:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=2)=[CH:31][CH:30]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].C(=O)([O-])[O-].[Na+].[Na+].CO[CH2:52][CH2:53][O:54][CH3:55]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH2:16]([C:5]1([CH2:18][CH3:19])[C:4]2[CH:3]=[C:2]([C:38]3[CH:39]=[CH:40][C:35]([C:32]4[CH:33]=[CH:34][C:29]([O:28][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:30][CH:31]=4)=[CH:36][CH:37]=3)[CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][C:8]([C:29]1[CH:30]=[CH:31][C:32]([C:35]3[CH:36]=[CH:37][C:53]([O:54][CH2:55][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH3:20])=[CH:52][CH:40]=3)=[CH:33][CH:34]=1)=[CH:9][CH:10]=2)[CH3:17]

Komponenten

7

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 35310452,7-Dibromo-9,9-diethylfluoreneHCID 108535444-Octyloxybiphenyl-4'-yl boronic acid

Produkt 1

HCID 219245109,9-Diethyl-2,7-bis(4-octyloxybiphenyl-4'-yl)fluoreneAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

Tetrakis(triphenylphosphine)palladium(0) (0.70 g, 0.0006 mol) was added to a stirred solution of 2,7-dibromo-9,9-diethylfluorene (4) (2.33 g, 0.0061 mol), 4-octyloxybiphenyl-4′-yl boronic acid (5.00 g, 0.0153 mol), 20% sodium carbonate solution (100 cm3) and 1,2-dimethoxyethane (150 cm3). The reaction mixture was heated under reflux overnight. Water (300 cm3) was added to the cooled reaction mixture and the product extracted into DCM (3×300 cm3). The combined organic extracts were washed with brine (2×150 cm3), dried (MgSO4)), filtered and the filtrate evaporated down under partially reduced pressure. The residue was purified by column chromatography on silica gel using DCM and hexane (30:70) as eluent and recrystallisation from ethanol and DCM to yield a white crystalline solid (3.10 g, 65%, m.pt. 146° C.).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux overnight
  3. extractionthe product extracted into DCM (3×300 cm3)
  4. washThe combined organic extracts were washed with brine (2×150 cm3)
  5. dry with materialdried (MgSO4)),
  6. filtrationfiltered
  7. customthe filtrate evaporated down under partially reduced pressure
  8. customThe residue was purified by column chromatography on silica gel
  9. customrecrystallisation from ethanol and DCM

Quellen und Nachweise

ORD-Eintrag
ord-9317a5bd136a48f1925889f6195fa0ae
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265163B2

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