Carbazole → Methyl 3,5-di(carbazol-9-yl)benzoate

HRID 1037513Notes

Reaction equation

HRID 1037513 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:9]=[C:10](I)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH:13]1[C:25]2[NH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]=2[CH:16]=[CH:15][CH:14]=1.C1O[CH2:42][CH2:41]OCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+]>ClC1C=CC=CC=1Cl>[CH:22]1[C:23]2[N:24]([C:2]3[CH:3]=[C:4]([CH:9]=[C:10]([N:24]4[C:42]5[CH:41]=[CH:14][CH:15]=[CH:16][C:17]=5[C:18]5[C:23]4=[CH:22][CH:21]=[CH:20][CH:19]=5)[CH:11]=3)[C:5]([O:7][CH3:8])=[O:6])[C:25]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18]=2[CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 6854CarbazoleHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 53435545Methyl 3,5-diiodobenzoate

Product 1

HCID 59638298Methyl 3,5-di(carbazol-9-yl)benzoate

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

To a solution of methyl 3,5-diiodobenzoate (3.0 g, 7.73 mmol), carbazole (3.0 g, 17.94 mmol), Cu (6.4 g, 100.71 mmol) and 18-crown-6 (65 mg, 0.25 mmol) in 1,2-dichlorobenzene (30.0 ml) was added potassium carbonate (12.6 g, 91.17 mmol) under nitrogen and stirring. The reaction was carried out at 180° C. for 10.5 hours. After cooling, the reaction mixture was filtrated. Then, the solid residues were carefully washed with THF. The THF and 1,2-dichlorobenzene were evaporated from the combined filtration solution. The product was purified by silica gel column chromatography using toluene as eluent. The final pure white product was obtained in 2.6 g (71.7%) by recrystallization from acetone/methanol.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtrated
  3. washThen, the solid residues were carefully washed with THF
  4. customThe THF and 1,2-dichlorobenzene were evaporated from the combined filtration solution
  5. customThe product was purified by silica gel column chromatography
  6. customThe final pure white product was obtained in 2.6 g (71.7%) by recrystallization from acetone/methanol

Sources & evidence

ORD record
ord-d756ae06c32f4532b2aa0edfc51ff2b5
Source dataset
uspto-grants-2013_10
Patent number
US08546505B2

Reaction notes

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