Sodium Carbonate → 3,6-DI-Tert-butyl-2,7-diphenyl-9H-fluorene

HRID 10942Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 10942
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.[C:24]1(B(O)O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCO.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:24]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:2]5[CH:14]=[CH:13][CH:12]=[CH:4][CH:3]=5)=[C:9]([C:19]([CH3:20])([CH3:22])[CH3:21])[CH:10]=4)[CH2:5][C:4]=3[CH:3]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Komponenten

8

Edukt 3

HCID 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 179,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a mixture of 2,7-dibromo-3,6-di-t-butylfluorene (0.96 g, 2.20 mmol) and Pd(PPh3)4 (260 mg, 0.22 mmol) in toluene (50 ml) was added a solution of phenylboronic acid (0.81 g, 6.63 mmol) in EtOH (10 ml) and a solution of Na2CO3 (1.5 g) in water (10 ml). The reaction mixture was stirred for 6 hours under reflux. The reaction mixture was quenched with water, extracted with ether, dried over MgSO4, and evaporated under vacuum to produce a residue which was purified by column chromatography (silica gel, hexane/CH2Cl2=5/1) to yield 2,7-diphenyl-3,6-di-t-butyl-fluorene (0.85 g, 90%). 1H NMR (CDCl3): δ 7.96 and 7.15 (each s, 2H, 1,8- and 4,5-H (Flu), 7.33 (m, 10H, Ph), 3.77 (s, 2H, H9), 1.27 (s, 18H, t-Bu).

Aufarbeitung

  1. temperatureunder reflux
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with ether
  4. dry with materialdried over MgSO4
  5. customevaporated under vacuum
  6. customto produce a residue which
  7. customwas purified by column chromatography (silica gel, hexane/CH2Cl2=5/1)

Quellen und Nachweise

ORD-Eintrag
ord-620740ab78764f6d8422ea034b41264b
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094938B1

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