Toluene → 3,6-Diformyl-9-p-tolylcarbazole

HRID 1597733Notes

Reaction equation

HRID 1597733 reaction equation
[C:1]1([CH3:20])[CH:6]=[CH:5][C:4]([N:7]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3C3C2=CC=CC=3)=[CH:3][CH:2]=1.CN([CH:24]=[O:25])C.P(Cl)(Cl)(Cl)=[O:27].[C:31]1([CH3:37])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>[Cl-].[Zn+2].[Cl-].C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH:37]([C:31]1[CH:36]=[CH:35][C:34]2[N:7]([C:4]3[CH:3]=[CH:2][C:1]([CH3:20])=[CH:6][CH:5]=3)[C:19]3[C:14]([C:33]=2[CH:32]=1)=[CH:15][C:16]([CH:24]=[O:25])=[CH:17][CH:18]=3)=[O:27]

Participants

7

Reactant 4

HCID 1140TolueneHCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 157986519-(p-Tolyl)carbazole

Product 1

HCID 189319013,6-Diformyl-9-p-tolylcarbazoleYield 24.1%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 21584019Toluene ethylacetateSolvent

Procedure

50.0 g (0.19 mol) of 9-p-tolylcarbazole (4c), 100.0 g (1.37 mol) of DMF, 51.8 g (0.38 mol) of zinc chloride, 174.8 g (1.14 mol) of phosphorus oxychloride and 500 g of toluene were allowed to react and after treated in the same manner as with Example 1 (1), and treated by silica gel column chromatography (eluent: toluene/ethyl acetate=9/1 by volume) to obtain 16.65 g of crude crystals. These crystals were recrystallized from toluene to obtain 14.33 g of 3,6-diformyl-9-p-tolylcarbazole.

Workup

  1. customto react
  2. customto obtain 16.65 g of crude crystals
  3. customThese crystals were recrystallized from toluene

Sources & evidence

ORD record
ord-24597f83dc354d3bb406c8b84fea6eaf
Source dataset
uspto-grants-1998_04
Patent number
US05736284

Reaction notes

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