Phosphorus oxychloride → 2-Chloro-4-(4-fluorophenyl)-7-methylquinoline

HRID 2422549Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2422549
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([CH3:18])=[CH:15][CH:16]=3)[N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:21])=O.C([O-])(O)=O.[Na+]>>[Cl:21][C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:17]2[C:12](=[CH:13][C:14]([CH3:18])=[CH:15][CH:16]=2)[N:11]=1

Komponenten

4

Edukt 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 574378424-(4-Fluorophenyl)-7-methylquinoline

Produkt 1

HCID 866219782-Chloro-4-(4-fluorophenyl)-7-methylquinoline

Versuchsvorschrift

A solution of 4-(4-fluorophenyl)-7-methylquinoline (3.09 g, 12.2 mmol) in phosphorus oxychloride (8 mL, 85.8 mmol) was stirred 30 min. at 90° C. The mixture was poured slowly into an aqueous saturated solution of NaHCO3 and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduce pressure. Purification on silica gel (eluting with acetone/dichloromethane/hexanes, 1:70:29) gave the title compound. MS (+ESI): 271 (M+H)+.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification on silica gel (eluting with acetone/dichloromethane/hexanes, 1:70:29)

Quellen und Nachweise

ORD-Eintrag
ord-70b02feae16d4e10bec38f51d393c9a6
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960409B2

Notizen zur Reaktion

Wird geladen…