Reaktion #71490

Reaktionsgleichung

Sulfuryl chloride

5-(2-fluoro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid ethyl ester

→

title compound

Ausbeute 66.2%

5-(2-Chloro-6-fluoro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylicacid ethyl ester

Ausbeute 66.2%

Lösungsmittel

CH3CN

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigequenched by addition of a saturated solution of NaHCO3
2. 2
   Einengenconcentrated
3. 3
   workup.ADDITIONThe residue was diluted in EtOAc
4. 4
   SonstigeThe aqueous phase was separated
5. 5
   Extraktionextracted with EtOAc
6. 6
   WaschenThe combined organic layers were washed with H2O and brine
7. 7
   Trocknendried (Na2SO4)
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated
10. 10
    SonstigeThe residue was purified by silica gel column chromatography (Hex/EtOAc, 3:2)

Vorschrift

Sulfuryl chloride (75 μL, 0.93 mmol) was added dropwise to a cold (−20° C.) solution of 5-(2-fluoro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid ethyl ester (Step 176.3) (330 mg, 0.93 mmol) in CH3CN (6 mL). The reaction mixture was stirred for 10 min at −20° C., quenched by addition of a saturated solution of NaHCO3, and concentrated. The residue was diluted in EtOAc and a saturated solution of NaHCO3. The aqueous phase was separated and extracted with EtOAc. The combined organic layers were washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (Hex/EtOAc, 3:2) to provide 240 mg of the title compound as a white solid. Title compound: ESI-MS: 390.1 [M+H]+; tR=3.98 min (System 1); TLC: Rf=0.15 (Hex/EtOAc, 3:2).

Quelle