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

HRID 420023Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 420023
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 afford the residue which was purified by column chromatography (silica gel, hexane/CH2Cl2=5/1) to produce 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 afford the residue which
  7. customwas purified by column chromatography (silica gel, hexane/CH2Cl2=5/1)

Quellen und Nachweise

ORD-Eintrag
ord-0e3c1622f4754cbba46c36b1bb5dcc54
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093418B2

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