1,3-Dibromobenzene → 1-(3-(3-bromophenyl)-9H-carbazol-9-yl)ethanone

HRID 1957899Notes

Reaction equation

HRID 1957899 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][C:12]3[N:13]([C:22](=[O:24])[CH3:23])[C:14]4[C:19]([C:20]=3[CH:21]=2)=[CH:18][CH:17]=[CH:16][CH:15]=4)O1.[Br:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29](Br)[CH:28]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:26][C:27]1[CH:28]=[C:29]([C:9]2[CH:21]=[CH:20][C:12]3[N:13]([C:22](=[O:24])[CH3:23])[C:14]4[C:19]([C:11]=3[CH:10]=2)=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:30]=[CH:31][CH:32]=1

Participants

7

Reactant 3

HCID 79271,3-DibromobenzeneHCID 11430Potassium CarbonateHCID 712362521-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazol-9-yl)ethanone

Product 1

HCID 712363961-(3-(3-bromophenyl)-9H-carbazol-9-yl)ethanoneYield 23%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-fa11a77dab5741409ecc2b3c321447b0
Source dataset
uspto-grants-2013_04
Patent number
US08409729B2

Reaction notes

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