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

HRID 630579Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 630579
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(B(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 66827Phenylboronic AcidHCID 135475422,7-Dibromo-3,6-DI-tert-butyl-9H-fluorene

Produkt 1

HCID 219826953,6-DI-Tert-butyl-2,7-diphenyl-9H-fluoreneAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, 8.15 g (18.7 mmol) of 2,7-dibromo-3,6-di-tert-butylfluorene, 1.08 g (0.93 mmol) of Pd(PPh3), and 120 mL of dry 1,2-dimethoxyethane were put into a 300-mL three-necked flask and then stirred at room temperature for 20 minutes. To this solution, 20 mL of a solution of 5.01 g (41.1 mmol) of phenylboronic acid in ethanol was added, the resulting solution was stirred at room temperature for 20 minutes, and then 37.4 mL (74.8 mmol) of an aqueous solution of 2.0-M sodium carbonate was added thereto. Then, the product was heated for 18 hours under reflux, left to stand to cool, and quenched with dilute hydrochloric acid in an ice bath. Ether was added thereto, the soluble part in ether was extracted, and the organic layer was washed twice with an aqueous solution of saturated sodium hydrogen carbonate, further twice with water, and further twice with a saturated salt solution and then dehydrated with magnesium sulfate. The solvent was distilled off, and then the obtained solid was separated by column chromatography to obtain an objective (amount: 4.36 g and yield: 54%).

Aufarbeitung

  1. stirringthe resulting solution was stirred at room temperature for 20 minutes
  2. temperatureThen, the product was heated for 18 hours
  3. temperatureunder reflux
  4. waitleft
  5. temperatureto cool
  6. customquenched with dilute hydrochloric acid in an ice bath
  7. additionEther was added
  8. extractionthe soluble part in ether was extracted
  9. washthe organic layer was washed twice with an aqueous solution of saturated sodium hydrogen carbonate, further twice with water
  10. distillationThe solvent was distilled off
  11. customthe obtained solid was separated by column chromatography
  12. customto obtain an objective (amount: 4.36 g and yield: 54%)

Quellen und Nachweise

ORD-Eintrag
ord-8320975dc74c4fd982e2aa394a53d913
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09315602B2

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