Reacción #2045081

Ecuación de reacción

1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazol-9-yl)ethanone

1,3-dibromobenzene

K2CO3

→

1-(3-(3-bromophenyl)-9H-carbazol-9-yl)ethanone

Rendimiento 23.0%

Disolventes

toluene

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe organic phase was isolated
2. 2
   Otrothe solvent was evaporated
3. 3
   OtroThe residue was purified by column chromatography on silica gel with hexane/DCM (1/1

Procedimiento

A mixture solution of 1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazol-9-yl)ethanone (10.00 g, 29.8 mmol), 1,3-dibromobenzene (17.59 g, 74.6 mmol), Pd(PPh3)4 (0.689 g, 0.597 mmol) and K2CO3 (12.37 g, 89 mmol) in toluene (100 mL) and water (20 mL) was refluxed under N2 overnight. After cooling to room temperature, the organic phase was isolated and the solvent was evaporated. The residue was purified by column chromatography on silica gel with hexane/DCM (1/1, v/v) as eluent to yield 1-(3-(3-bromophenyl)-9H-carbazol-9-yl)ethanone (2.5 g, 23%) as a white solid.

Fuente