Reaktion #75705

Reaktionsgleichung

2-Chloroquinoline-4-carboxylic acid methyl ester

potassium fluoride

→

2-fluoroquinoline-4-carboxylic acid methyl ester

Ausbeute 66.3%

Lösungsmittel

dichloromethane water

dimethylsulfone

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled to room temperature
2. 2
   Sonstigethe organic phase separated
3. 3
   Sonstigesolvent removed at reduced pressure
4. 4
   Sonstigethe residue column chromatographed (silica gel, dichloromethane eluant)

Vorschrift

2-Chloroquinoline-4-carboxylic acid methyl ester (1.14 g) in dimethylsulfone (4.0 g) was treated with potassium fluoride (2.5 g) and heated at 180° C. for 1 h. The reaction mixture was cooled to room temperature, diluted with dichloromethane:water (1:1, 200 ml), the organic phase separated, solvent removed at reduced pressure and the residue column chromatographed (silica gel, dichloromethane eluant) to give 2-fluoroquinoline-4-carboxylic acid methyl ester (0.7 g). 1H NMR (CDCl3) δ: 3.99 (3H, s), 7.57 (2H, m), 7.72 (1H, m), 7.95 (1H, d, J=8.5 Hz), 8.67 (1H, d, J=8.4 Hz). m/z (API+): 205 (MH+).

Quelle