Cesium fluoride → 2-(4'-Chloro-4-ethyl-2'-methylbiphen-3-yl)-4,4-dimethyl-cyclohexane-1,3-dione

HRID 400382

Reaktionsgleichung

Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:18][CH3:19])=[C:6]([CH:8]2[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[CH2:11][CH2:10][C:9]2=[O:17])[CH:7]=1.[CH3:20][C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1B(O)O.[F-].[Cs+]>COCCOC.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]>[Cl:27][C:25]1[CH:24]=[CH:23][C:22]([C:2]2[CH:3]=[CH:4][C:5]([CH2:18][CH3:19])=[C:6]([CH:8]3[C:13](=[O:14])[C:12]([CH3:16])([CH3:15])[CH2:11][CH2:10][C:9]3=[O:17])[CH:7]=2)=[C:21]([CH3:20])[CH:26]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A mixture of 2-(5-bromo-2-ethylphenyl)-4,4-dimethylcyclohexane-1,3-dione (0.194 g, 0.6 mmol), 2-methyl-4-chloro-phenylboronic acid (0.153 g, 0.9 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (complex with dichloromethane 1:1) (80 mg, 0.098 mmol) and cesium fluoride (0.608 g, 4 mmol) are stirred together in 1,2-dimethoxyethane (4 ml) and the reaction mixture is heated at 80° C. overnight. The warm reaction mixture is filtered, washing the filter cake with 9:1 dichloromethane:methanol. The mixture is concentrated under reduced pressure and the residue is purified by column chromatography on silica gel to give 2-(4′-chloro-4-ethyl-2′-methylbiphen-3-yl)-4,4-dimethyl-cyclohexane-1,3-dione.

Aufarbeitung

customThe warm reaction mixture
filtrationis filtered
washwashing the filter cake with 9:1 dichloromethane
concentrationThe mixture is concentrated under reduced pressure
customthe residue is purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag: ord-2b6c5141eef649918800f0a6fff9105f
Quelldatensatz: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08741806B2

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