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

HRID 909116Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 909116
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-fluoreneAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

In a nitrogen atmosphere, 8.15 g (18.7 mmol) of 2,7-dibromo-3,6-di-tert-butyl-fluorene and 1.08 g (0.93 mmol) of Pd(PPh3) were added to a 300 mL three-neck flask, and then 120 mL of dehydrated 1,2-dimethoxyethane was added and the mixture was stirred at room temperature for 20 min. To the solution obtained, 20 mL of ethanol solution containing 5.01 g (41.1 mmol) of phenyl boric acid was added and the mixture was stirred at room temperature for 20 min, and then 37.4 mL (74.8 mmol) of a 2.0 mol/L sodium carbonate aqueous solution was added. Thereafter, the mixture was refluxed while heating for 18 hr and cooled spontaneously, and then quenched with dilute hydrochloric acid in an ice bath. The soluble part was extracted by adding ether, and the organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution twice, with water twice and with saturated brine twice, and then dried with magnesium sulfate. Thereafter, the solvent was distilled off and the resulting solid was separated with a column chromatography to prepare an aimed product (in an amount of 4.36 g in a yield of 54%). The identification of the aimed product was carried out by 1H-NMR and FD-MS spectrum.

Aufarbeitung

  1. customTo the solution obtained
  2. additionwas added
  3. stirringthe mixture was stirred at room temperature for 20 min
  4. temperatureThereafter, the mixture was refluxed
  5. temperaturewhile heating for 18 hr
  6. temperaturecooled spontaneously
  7. customquenched with dilute hydrochloric acid in an ice bath
  8. extractionThe soluble part was extracted
  9. additionby adding ether
  10. washthe organic layer was washed with a saturated sodium hydrogen carbonate aqueous solution twice
  11. dry with materialwith water twice and with saturated brine twice, and then dried with magnesium sulfate
  12. distillationThereafter, the solvent was distilled off
  13. customthe resulting solid was separated with a column chromatography
  14. customto prepare an aimed product (in an amount of 4.36 g in a yield of 54%)

Quellen und Nachweise

ORD-Eintrag
ord-0354c7c9b4c94c0a81f6c42dac01e5ea
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017705B2

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