Toluene → 2,7-Diphenyl-9H-carbazole

HRID 1776066Notes

Reaction equation

HRID 1776066 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].BrC1[CH:27]=[CH:26][C:25]2[C:24]3[C:19](=[CH:20][C:21](Br)=[CH:22][CH:23]=3)[NH:18][C:17]=2[CH:16]=1.[C:29]1(B(O)O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(O)C>[C:1]1([C:7]2[CH:27]=[CH:26][C:25]3[C:24]4[C:19](=[CH:20][C:21]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)=[CH:22][CH:23]=4)[NH:18][C:17]=3[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 111515032,7-Dibromocarbazole

Product 1

HCID 667173012,7-Diphenyl-9H-carbazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add 80 ml of toluene, 20 ml of ethanol, and 40 g of 2M sodium carbonate aqueous solution to 6.50 g of 2,7-dibromocarbazole, 7.32 g of phenyl boronic acid, 0.734 g of tetrakis triphenyl phosphine palladium; reflux the mixture for three hours while heating in nitrogen atmosphere followed by cooling down to room temperature; filter the mixture to remove insoluble matters; distill away the solvent to obtain 4.15 g of pale bark powder of 2,7-diphenyl carbazole; mix 4.01 g of the thus obtained 2,7-diphenyl carbazole, 4.37 g of 4-(8-hydroxyoctyloxy)iodine benzene, 3.45 g of potassium carbonate, 0.5 g of copper powder, and 20 ml of nitrobenzene; reflux the mixture for seven hours while heating in nitrogen atmosphere followed by cooling down to room temperature; filter the mixture to remove insoluble matters; distill away the solvent; next, refine the resultant with silica gel column chromatography using a liquid mixture of ethyl acetate and hexane as an eluting solution to obtain 2.0 g of a pale bark oily matter of 2.7-diphenyl-N-[4-(8-hydroxyoctyloxyphenyl)]carbazole; and then, tosylate, thioacetylate, and hydrolyze the thus obtained 2.7-diphenyl-N-[4-(8-hydroxyoctyloxyphenyl)]carbazole in the same manner as in Synthesis of Carbazole Derivative 2 to obtain 2,7-diphenyl-N-[4-(8-mercaptooctyloxyphenyl)]carbazole (hereinafter referred to as carbazole derivative 5) having a colorless needle-like crystal represented by the chemical structure 11.

Workup

  1. temperaturereflux the mixture for three hours
  2. temperaturewhile heating in nitrogen atmosphere
  3. filtrationfilter the mixture
  4. customto remove insoluble matters
  5. distillationdistill away the solvent

Sources & evidence

ORD record
ord-ef9a23af731743a9a3a8b51f0fcb1ddf
Source dataset
uspto-grants-2016_02
Patent number
US09263682B2

Reaction notes

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