Toluene → 5-(7-dibutylamino-9H-fluoren-2-yl)-thiophene-2-carbaldehyde

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Reaktionsgleichung

Br[C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][C:9]([N:15]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][CH3:19])=[CH:10][C:11]=3[CH2:12]2)=[CH:4][CH:3]=1.[CH:24]([C:26]1[S:30][C:29](B(O)O)=[CH:28][CH:27]=1)=[O:25].C(=O)([O-])[O-].[K+].[K+].C1(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].CO>[CH2:16]([N:15]([CH2:20][CH2:21][CH2:22][CH3:23])[C:9]1[CH:10]=[C:11]2[C:6]([C:5]3[CH:4]=[CH:3][C:2]([C:29]4[S:30][C:26]([CH:24]=[O:25])=[CH:27][CH:28]=4)=[CH:14][C:13]=3[CH2:12]2)=[CH:7][CH:8]=1)[CH2:17][CH2:18][CH3:19]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

Under N2 atmosphere, 0.37 parts of (7-bromo-9H-fluoren-2-yl)-dibutyl amine (11), 0.19 parts of 5-formyl-2-thiopheneboronic acid, 0.41 parts of potassium carbonate, and 0.16 parts of PdCl2(dppf) were added into 5 parts of toluene and 5 parts of CH3OH, followed by stirring and mixing. Then, the reaction mixture was heated to 60° C. and reacted for 18 hours. After the reaction mixture was quenched by water, using the diethyl ether to extract the product, and magnesium sulfate was used for dehydration. After removing the solvent, the residual was purified with chromatography method column by using dichloromethane/hexane co-solvent as an eluent, to obtain a compound (12a) of the present example. This compound was in a form of a tangerine solid, and the yield of this compound was 61%.

Aufarbeitung

additionmixing
customreacted for 18 hours
customAfter the reaction mixture was quenched by water
extractionto extract the product, and magnesium sulfate
customAfter removing the solvent
customthe residual was purified with chromatography method column

Quellen und Nachweise

ORD-Eintrag: ord-3e2a5e86bdab425d91eabff798068d49
Quelldatensatz: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08203068B2

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