1,2-Dimethoxyethane → 3,6-DI-Tert-butyl-2,7-diphenyl-9H-fluorene

HRID 1050648Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1050648
Br[C:2]1[C:14]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8](Br)=[C:9]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.CO[CH2:26][CH2:27]OC.[C:30]1(OB(O)O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[C:30]1([C:2]2[C:14]([C:15]([CH3:17])([CH3:18])[CH3:16])=[CH:13][C:12]3[C:11]4[C:6](=[CH:7][C:8]([C:27]5[CH:26]=[CH:4][CH:3]=[CH:2][CH:14]=5)=[C:9]([C:19]([CH3:20])([CH3:22])[CH3:21])[CH:10]=4)[CH2:5][C:4]=3[CH:3]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Komponenten

6

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 135475422,7-Dibromo-3,6-DI-tert-butyl-9H-fluorene

Produkt 1

HCID 219826953,6-DI-Tert-butyl-2,7-diphenyl-9H-fluorene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, a 300-mL three-necked flask was charged with 8.15 g (18.7 mmol) of 2,7-dibromo-3,6-ditert-butyl-fluorene and 1.08 g (0.93 mmol) of Pd(PPh3), and further charged with 120 mL of dehydrated 1,2-dimethoxyethane. The mixture was stirred at room temperature for 20 minutes. To this solution, 20 mL of an ethanol solution in which 5.01 g (41.1 mmol) of phenylboric acid was dissolved was added, and the mixture was then stirred at room temperature for 20 minutes. Thereafter, 37.4 mL (74.8 mmol) of a 2.0 mol/L aqueous solution of sodium carbonate was added. Subsequently, the mixture was heated to reflux for 18 hours, left to be naturally cooled, and quenched with dilute hydrochloric acid in an ice bath. Thereafter, ether was added to extract the soluble fraction, and the organic layer was washed two times with a saturated aqueous solution of sodium hydrogen carbonate, two times with water, and two times with saturated brine, and then dried over magnesium sulfate. Subsequently, the solvent was distilled off, and the resulting solids were subjected to separation by column chromatography to obtain a target product (yield 4.36 g (54%)). The target product was identified by 1H-NMR and FD-MS spectroscopy.

Aufarbeitung

  1. additionwas added
  2. stirringthe mixture was then stirred at room temperature for 20 minutes
  3. temperatureSubsequently, the mixture was heated
  4. temperatureto reflux for 18 hours
  5. waitleft
  6. temperatureto be naturally cooled
  7. customquenched with dilute hydrochloric acid in an ice bath
  8. additionThereafter, ether was added
  9. extractionto extract the soluble fraction
  10. washthe organic layer was washed two times with a saturated aqueous solution of sodium hydrogen carbonate, two times with water, and two times with saturated brine
  11. dry with materialdried over magnesium sulfate
  12. distillationSubsequently, the solvent was distilled off
  13. customthe resulting solids were subjected to separation by column chromatography
  14. customto obtain a target product (yield 4.36 g (54%))

Quellen und Nachweise

ORD-Eintrag
ord-9fb1dbd6b93a4777966a1cb7387925bd
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09382356B2

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