Sodium Iodide → 9-(3'-iodo-[1,1'-biphenyl]-3-yl)-9H-carbazole

HRID 1424768Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1424768
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N:14]3[C:26]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:20]4[C:15]3=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[I-:27].[Na+].CNC1CCCCC1NC>[Cu]I.O1CCOCC1>[I:27][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N:14]3[C:26]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:20]4[C:15]3=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 5238Sodium IodideHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamineHCID 588711539-(3'-bromo-[1,1'-biphenyl]-3-yl)-9H-carbazole

Produkt 1

HCID 903869089-(3'-iodo-[1,1'-biphenyl]-3-yl)-9H-carbazoleAusbeute 96,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

9-(3′-bromo-[1,1′-biphenyl]-3-yl)-9H-carbazole (9.50 g, 23.85 mmol), sodium iodide (7.15 g, 47.7 mmol), copper(I) iodide (1.363 g, 7.16 mmol), and dioxane (239 ml) were added into a 500 mL 3-necked flask. N1,N2-dimethylcyclohexane-1,2-diamine (1.881 ml, 11.93 mmol) was added. The reaction mixture was heated and refluxed overnight. After completion of the reaction, the reaction mixture was cooled to room temperature. The reaction mixture was filtered through a pad of Celite® and washed several times with DCM. The solvent are evaporated in vacuum. The crude material was purified by column chromatography using hexane and DCM (75/25) and gradually increasing DCM to a ratio of hexane/DCM 50/50. The product was further purified by trituration from methanol. 9-(3′-iodo-[1,1′-biphenyl]-3-yl)-9H-carbazole (10.2 g, 22.91 mmol, 96% yield) was obtained as a white solid.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperaturerefluxed overnight
  3. customAfter completion of the reaction
  4. filtrationThe reaction mixture was filtered through a pad of Celite®
  5. washwashed several times with DCM
  6. customThe solvent are evaporated in vacuum
  7. customThe crude material was purified by column chromatography
  8. customThe product was further purified by trituration from methanol

Quellen und Nachweise

ORD-Eintrag
ord-e51b2b945f4a49018deab1531805da4c
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927749B2

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