Toluene → HCID 86712053, Verbindung

HRID 1755525

Reaktionsgleichung

Br[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[C:5]([CH3:17])([CH3:16])[C:4]=2[CH:3]=1.[C:18]1(C)[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH:24][C:25]1[CH:30]=CC=C[C:26]=1C.[CH3:33][C:34]([CH3:37])([O-])[CH3:35].[Na+].[C:39]1(C)C=CC=CC=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Br:15][C:8]1[CH:7]=[C:6]2[C:11]([C:12]3[CH:13]=[CH:14][C:2]([N:24]([C:19]4[CH:18]=[CH:23][C:22]([CH3:39])=[CH:21][CH:20]=4)[C:25]4[CH:26]=[CH:35][C:34]([CH3:37])=[CH:33][CH:30]=4)=[CH:3][C:4]=3[C:5]2([CH3:16])[CH3:17])=[CH:10][CH:9]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A mixture of 2,7-dibromo-9,9-dimethyl-9H-fluorene (31.64 g, 89.87 mmol), ditolylamine (8.865 g, 44.9 mmol), Pd(dppf)Cl2 (1.644 g, 2.25 mmol) and sodium tert-butoxide (10.796 g, 112.3 mmol) in toluene 400 mL was degassed and heated at about 80° C. overnight. The resulting mixture was poured into ethyl acetate (500 mL). After the precipitate was filtered off, the solution was washed with water and brine, dried over Na2SO4, loaded on silica gel and purified by flash column (hexane to hexanes/dichloromethane 99:1 to 95:5 gradients). After removal of solvent and recrystallization in dichloromethane/hexanes, a white solid (Compound 32) was obtained (14.0169 g, in 66.6% yield).

Aufarbeitung

customwas degassed
additionThe resulting mixture was poured into ethyl acetate (500 mL)
filtrationAfter the precipitate was filtered off
washthe solution was washed with water and brine
dry with materialdried over Na2SO4
custompurified by flash column (hexane to hexanes/dichloromethane 99:1 to 95:5 gradients)
customAfter removal of solvent and recrystallization in dichloromethane/hexanes

Quellen und Nachweise

ORD-Eintrag: ord-dbcc9cdabf984bc6a8ebafc47ca3c079
Quelldatensatz: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09172051B2

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