Water → 2-Methyl-4-phenoxy-8-(2,4,6-trimethylphenyl)-quinoline

HRID 1700115Notizen

Reaktionsgleichung

[CH3:1][C:2]1[CH:11]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]2[C:4](=[C:5](Br)[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:20][C:21]1[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[C:22]=1B(O)O.O>COCCOC.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>[CH3:1][C:2]1[CH:11]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]2[C:4](=[C:5]([C:22]3[C:23]([CH3:28])=[CH:24][C:25]([CH3:27])=[CH:26][C:21]=3[CH3:20])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

Part C: To a solution of 5.2 g (16.5 mmol) of 2-methyl-4-phenoxy-8-bromo-quinoline in 175 ml DME-water (6:1), 3.3 g (20 mmol) of 2,4,6-tri-methyl-phenyl-boronic acid, 12.6 g (40 mmol) of Ba(OH)2.8H2O and 0.46 g (0.4 mmol) of tetrakis(triphenylphosphine)palladium were added. After heating at 80° C. for 16 hours the mixture was cooled to room temperature, water was added and the mixture was extracted with CH2Cl2. The organic layer was dried over magnesium sulphate and concentrated in vacuo. The product was purified on a silicagel column using CH2Cl2 as the eluent. A total of 4.2 g of 2-methyl-4-phenoxy-8-(2,4,6-trimethylphenyl)-quinoline was obtained (73% yield)

Aufarbeitung

temperaturewas cooled to room temperature
extractionthe mixture was extracted with CH2Cl2
dry with materialThe organic layer was dried over magnesium sulphate
concentrationconcentrated in vacuo
customThe product was purified on a silicagel column

Quellen und Nachweise

ORD-Eintrag: ord-b35a9f33effd4194a0f6070a95547eee
Quelldatensatz: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06350750B1

Notizen zur Reaktion

Wird geladen…