Potassium Carbonate → 3-Bromo-9-phenylcarbazole

HRID 716597Notes

Reaction equation

HRID 716597 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.I[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>ClC1C=CC=CC=1Cl.[Cu]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 2855718-Crown-6HCID 2524463-Bromocarbazole

Product 1

HCID 189426243-Bromo-9-phenylcarbazoleYield 119.3%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 72391,2-DichlorobenzeneSolvent

Procedure

3Bromo-9H-carbazole (10.0 g, 40.6 mmol), iodobenzene (20.7 g, 101.6 mmol), potassium carbonate (28.1 g, 203.2 mmol), copper (2.58 g, 40.6 mmol), 18-crown-6 (10.7 g, 40.6 mmol) in o-dichlorobenzene (400 mL) were stirred and degassed with nitrogen for 15 minutes. The reaction was refluxed overnight. The reaction mixture was filtered Celite®, washed with toluene and the filtrate was concentrated under vacuum. It was then column chromatographed with 20% DCM/hexane to obtain 15.6 g (81%) of the desired product as a white solid.

Workup

  1. customdegassed with nitrogen for 15 minutes
  2. temperatureThe reaction was refluxed overnight
  3. filtrationThe reaction mixture was filtered Celite®
  4. washwashed with toluene
  5. concentrationthe filtrate was concentrated under vacuum
  6. customcolumn chromatographed with 20% DCM/hexane

Sources & evidence

ORD record
ord-6c543f50e3b14fba9d4de3419428bc56
Source dataset
uspto-grants-2015_11
Patent number
US09190623B2

Reaction notes

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