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

HRID 1721837Notes

Reaction equation

HRID 1721837 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]>[CH3:27][O:26][C:24]([CH2:23][CH2:22][C:5]1([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:4]2[CH:3]=[C:2]([N:40]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:41]3[CH:42]=[C:43]([CH3:47])[CH:44]=[CH:45][CH:46]=3)[CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][C:8]([N:40]([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:41]1[CH:42]=[C:43]([CH3:47])[CH:44]=[CH:45][CH:46]=1)=[CH:9][CH:10]=2)=[O:25]

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 17.9 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 SoltrolR 220 was mechanically stirred and heated to 150° C. under a nitrogen atmosphere. Fifteen (15.0) grams of molten N-phenyl-m-toluidine was then added dropwise at 150° C. 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. Subsequently, the combined filtrate was evaporated under reduced pressure to yield a brown residue, which was purified by column chromatography on silica gel to afford 15.2 grams of pure 9,9-bis[2-(methoxycarbonyl)ethyl]-2,7bis(phenyl-m-tolylamino)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. customSubsequently, the combined filtrate was evaporated under reduced pressure
  7. customto yield a brown residue, which
  8. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-072b5f98622a447f9e704f9cf11c7638
Source dataset
uspto-grants-1989_08
Patent number
US04853308

Reaction notes

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