Cesium fluoride → HCID 22245418, Verbindung

HRID 1178318Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1178318
[F-].[Cs+].Br[C:4]1[CH:17]=[CH:16][C:15]2[C:6](=[CH:7][C:8]3[C:13]([CH:14]=2)=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:5]=1.C([Sn](CCCC)(CCCC)[C:23]1[S:27][C:26]([C:28]2[S:29][C:30]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[CH:31][CH:32]=2)=[CH:25][CH:24]=1)CCC.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH:5]1[C:6]2[C:15](=[CH:14][C:13]3[C:8]([CH:7]=2)=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:16]=[CH:17][C:4]=1[C:23]1[S:27][C:26]([C:28]2[S:29][C:30]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[CH:31][CH:32]=2)=[CH:25][CH:24]=1

Komponenten

7

Edukt 4

HCID 25953Cesium fluorideHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 10744982Stannane, tributyl(5'-hexyl[2,2'-bithiophen]-5-yl)-HCID 123460992-Bromoanthracene

Produkt 1

HCID 22245418HCID 22245418, VerbindungAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A vessel was charged with Pd2(dba)3 (77 mg, 84 μmol, 2 mol %), CsF (1.41 g, 9.29 mmol), 2-bromoanthracene (1.09 g, 4.22 mmol), 1,4-dioxane (20 mL), 5-(tri-n-butylstannyl)-5′-hexyl-2,2′-bithiophene (2.28 g, 4.22 mmol), and P(t-Bu)3 (0.74 mL of a 10 wt % solution in hexanes, 0.25 mmol). The mixture was heated at 95° C. for 36 h and then the volatile materials were removed under reduced pressure. The residue was extracted with 450 mL methylene chloride and the filtered extract was washed with 2×150 mL of brine. After drying with MgSO4, the bright orange solution was filtered, concentrated, and then cooled overnight at −35° C. Bright orange product (1.35 g, 75%) was isolated by filtration and dried under vacuum. The material may be purified further by gradient sublimation at a source temperature of 175-200° C. 1H NMR was consistent with the desired structure. UV-vis spectrum in CHCl3, 17.3 μg/mL: λmax (ε), 246 (53,500), 259 (54,700), 342 (40,200), 356 (42,900), 397 (27,600). ΔEopt˜2.8 eV. Fluorescence spectrum in CHCl3, excitation at 400 nm: λmax=464 (1.4×106 CPS). DSC (20° C./min): 204° C., (mp, ΔH=36 Jg−1).

Aufarbeitung

  1. customthe volatile materials were removed under reduced pressure
  2. extractionThe residue was extracted with 450 mL methylene chloride
  3. extractionthe filtered extract
  4. washwas washed with 2×150 mL of brine
  5. dry with materialAfter drying with MgSO4
  6. filtrationthe bright orange solution was filtered
  7. concentrationconcentrated
  8. temperaturecooled overnight at −35° C

Quellen und Nachweise

ORD-Eintrag
ord-a3b234e1612d4a639a3918ddcd9a41cc
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07276395B2

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