Toluene → 6-Bromo-4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline

HRID 526835Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 526835
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7](Cl)[C:6]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1)=[C:5]2[Cl:24].C1(C)C=CC=CC=1.[CH3:32][O-:33].[Na+].[Al]>CCCCCC.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:33][CH3:32])[C:6]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1)=[C:5]2[Cl:24]

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 5359268AluminumHCID 10942334Sodium MethoxideHCID 867156286-Bromo-2,4-dichloro-3-(4-(trifluoromethyl)benzyl)quinoline2×

Produkt 1

HCID 867156276-Bromo-4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226440Methylenechloride HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a 1 L flask containing 6-bromo-2,4-dichloro-3-(4-(trifluoromethyl)benzyl)quinoline (32.5 g, 74.7 mmol, Intermediate 5: step c) was added toluene (550 mL) followed by solid sodium methoxide (40 g, 740 mmol, 97% purity) at room temperature. The suspension was stirred at reflux (˜118° C.) in an aluminum mantle. TLC (50% hexane-DCM) and HPLC after 5.5 hours showed the reaction to be complete. The reaction mixture was filtered through Celite® while still warm (˜80° C.) and rinsed with warm toluene (˜70° C., 500 mL). The colorless filtrate was concentrated which then solidified to afford the title compound as an off white solid.

Aufarbeitung

  1. customthe reaction
  2. filtrationThe reaction mixture was filtered through Celite®
  3. washrinsed with warm toluene (˜70° C., 500 mL)
  4. concentrationThe colorless filtrate was concentrated which

Quellen und Nachweise

ORD-Eintrag
ord-d17bbea1afb0401bbb779c9c475c1fe3
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346782B2

Notizen zur Reaktion

Wird geladen…