反应 #2045081

ord-fa11a77dab5741409ecc2b3c321447b0

反应方程式

CC(=O)n1c2ccccc2c2cc(B3OC(C)(C)C(C)(C)O3)ccc21
1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazol-9-yl)ethanone
Brc1cccc(Br)c1
1,3-dibromobenzene
O=C([O-])[O-].[K+].[K+]
K2CO3
CC(=O)n1c2ccccc2c2cc(-c3cccc(Br)c3)ccc21
1-(3-(3-bromophenyl)-9H-carbazol-9-yl)ethanone
收率 23.0%

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

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

实验过程

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.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US08409729B2uspto-grants-2013_04