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Toluene → 4-(9,9-Dioctyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-9H-fluoren-2-YL)-N,N-diphenylaniline

HRID 11189
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 11189
Br[C:2]1[CH:20]=[CH:19][C:5]([N:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH2:21]([C:29]1([CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH3:67])[C:41]2[CH:40]=[C:39]([B:42]3[O:46][C:45]([CH3:48])([CH3:47])[C:44]([CH3:50])([CH3:49])[O:43]3)[CH:38]=[CH:37][C:36]=2[C:35]2[C:30]1=[CH:31][C:32](B1OC(C)(C)C(C)(C)O1)=[CH:33][CH:34]=2)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].CC(C)=O.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.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.CCCCCC.O>[CH2:60]([C:29]1([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:30]2[CH:31]=[C:32]([C:2]3[CH:20]=[CH:19][C:5]([N:6]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)=[CH:4][CH:3]=3)[CH:33]=[CH:34][C:35]=2[C:36]2[C:41]1=[CH:40][C:39]([B:42]1[O:43][C:44]([CH3:49])([CH3:50])[C:45]([CH3:47])([CH3:48])[O:46]1)=[CH:38][CH:37]=2)[CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH3:67]
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Komponenten

11

Edukt 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 6428384-BromotriphenylamineHCID 219820749,9-Dioctylfluorene-2,7-diboronic acid bis(pinacol) ester

Produkt 1

HCID 219820994-(9,9-Dioctyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-9H-fluoren-2-YL)-N,N-diphenylaniline

Reagenzien, Katalysatoren, Lösungsmittel

6
HCID 21218Trioctylmethylammonium chlorideKatalysatorHCID 15220664Palladium--triphenylphosphane (1/1)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittelHCID 21889329Toluene hexaneLösungsmittel

Versuchsvorschrift

4-Bromo-N,N-diphenylaniline (19.44 g, 60 mmole, 1 equiv), 2-[9,9-dioctyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (76.9 g, 120 mmole, 2 equiv), Aliquat™ 336 (tricaprylylmethylammonium chloride) (6 g, 15 mmole, 0.25 equiv) and 2M sodium carbonate solution (75 mL, 150 mmole, 2.5 equiv) were added to 600 mL of toluene. This was purged with a stream of nitrogen for about 30 min. Under a nitrogen purge, tetrakis(triphenylphosphine palladium (0) (348 mg, 0.30 mmole, 0.005 equiv) was added. The reaction mixture was then refluxed for 16 hrs. The reaction was cooled to room temperature and water added. The organic layer was separated and washed with water followed by brine. Drying of the organic layer over Na2SO4 and evaporation of the solvent gave a light yellow solid. This was suspended in acetone and the mixture brought to reflux and then allowed to stand at room temperature overnight. Filtration of the solid and concentration of the filtrate gave a solid that was subjected to column chromatography (toluene:hexane 3:7) to give 4-[9,9-dioctyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluoren-2-yl]-N,N-diphenylaniline.

Aufarbeitung

  1. customThis was purged with a stream of nitrogen for about 30 min
  2. customUnder a nitrogen purge
  3. temperatureThe reaction mixture was then refluxed for 16 hrs
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialDrying of the organic layer over Na2SO4 and evaporation of the solvent
  7. customgave a light yellow solid
  8. temperatureto reflux
  9. filtrationFiltration of the solid and concentration of the filtrate
  10. customgave a solid

Quellen und Nachweise

ORD-Eintrag
ord-b2dbec03729041cdb275660146cddfe5
Quelldatensatz
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07094902B2

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