Reaktion #603675

Reaktionsgleichung

9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole

Compound 14

9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole

4-bromoiodobenzene

potassium carbonate

→

Compound 15

Ausbeute 44.0%

3-(4-bromophenyl)-9-phenyl-9H-carbazole

Ausbeute 44.0%

Lösungsmittel

dioxane water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas degassed
2. 2
   SonstigeThe organic phase was collected
3. 3
   Trocknendried over Na2SO4
4. 4
   Sonstigepurified by flash column (hexanes to hexane/ethyl acetate 90:1)
5. 5
   SonstigeThe main fraction was collected
6. 6
   Einengenconcentrated
7. 7
   Filtrationa precipitate was filtered

Vorschrift

A mixture of 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (Compound 14) (5.0 g, 13.5 mmol), 4-bromoiodobenzene (10.76 g, 38 mmol), Pd(PPh3)4 (0.5 g, 0.43 mmol) and potassium carbonate (K2CO3)(5.52 g, 40 mmol) in dioxane/water (80 mL/15 mL) was degassed and heated at about 100° C. overnight, then worked up with ethyl acetate/brine. The organic phase was collected, dried over Na2SO4, and purified by flash column (hexanes to hexane/ethyl acetate 90:1). The main fraction was collected, concentrated, and a precipitate was filtered to give a white solid (Compound 15) (2.35 g, in 44% yield). Confirmed by LCMS (APCI): calculated for C24H17BrN (M+H): 398; Found: 398.

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