Potassium Carbonate → 2,7-Bis(phenyl-m-tolylamino)-9,9-bis[2-(methoxycarbonyl)ethyl]fluorene

HRID 703400Notes

Reaction equation

HRID 703400 reaction equation
I[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8](I)=[CH:9][CH:10]=3)[C:5]([CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:34]1([NH:40][C:41]2[CH:46]=[CH:45][CH:44]=[C:43]([CH3:47])[CH:42]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>[Cu]>[C:34]1([N:40]([C:41]2[CH:42]=[C:43]([CH3:47])[CH:44]=[CH:45][CH:46]=2)[C:2]2[CH:14]=[CH:13][C:12]3[C:11]4[C:6](=[CH:7][C:8]([N:40]([C:34]5[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=5)[C:41]5[CH:42]=[C:43]([CH3:47])[CH:44]=[CH:45][CH:46]=5)=[CH:9][CH:10]=4)[C:5]([CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:4]=3[CH:3]=2)[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 14569N-(3-Methylphenyl)anilineHCID 198174132,7-Diiodo-9,9-bis[2-(methoxycarbonyl)ethyl]fluorene

Product 1

HCID 145978792,7-Bis(phenyl-m-tolylamino)-9,9-bis[2-(methoxycarbonyl)ethyl]fluorene

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Conditions

Temperature
150 °C

Procedure

A mixture of 17.0 grams of 2,7-diiodo-9,9-bis[2-(methoxycarbonyl)ethyl]fluorene, 4.3 grams of copper bronze, 12.5 grams of potassium carbonate in 30 milliliters of Soltrol 220 was mechanically stirred and heated to 150° C. under a nitrogen atmosphere. Fifteen (15.0) grams of molten N-phenyl-m-toluidine was added dropwise at this temperature. After addition, the resulting mixture was heated at 210° C. under reflux for 24 hours. The hot reaction mixture was filtered, and the filter cake was washed several times with hot cyclohexane. The combined filtrate was evaporated under reduced pressure to give a brown residue which was purified by column chromatography on silica gel to afford 15.2 grams of pure 2,7-bis(phenyl-m-tolylamino)-9,9-bis[2-(methoxycarbonyl)ethyl]-fluorene, melting point 159° to 160° C.

Workup

  1. additionAfter addition
  2. temperaturethe resulting mixture was heated at 210° C.
  3. temperatureunder reflux for 24 hours
  4. filtrationThe hot reaction mixture was filtered
  5. washthe filter cake was washed several times with hot cyclohexane
  6. customThe combined filtrate was evaporated under reduced pressure
  7. customto give a brown residue which
  8. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-367e8f88bdd0403fb702df7298c72ca5
Source dataset
uspto-grants-1991_01
Patent number
US04983482

Reaction notes

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