Reaktion #42543

Reaktionsgleichung

7-bromo-1-chloroisoquinoline

butylmagnesium chloride

→

7-bromo-1-butylisoquinoline

Ausbeute 24.4%

Lösungsmittel

ethyl acetate

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction maintained
2. 2
   Temperaturat reflux for 2 h
3. 3
   Waschenwashed with saturated sodium bicarbonate, water, and saturated sodium chloride
4. 4
   Trocknendried (sodium sulfate)
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   Sonstigeto give an brown oil
8. 8
   SonstigePurification by flash column chromatography (silica, 1-10% ether/hexanes)

Vorschrift

To a refluxing solution of 7-bromo-1-chloroisoquinoline (4.85 g, 23.28 mmol) in diethyl ether (75 mL) was added butylmagnesium chloride (17.8 mL, 2.0 M ether, 35.6 mmol) and the reaction maintained at reflux for 2 h. The reaction mixture was cooled to room temperature, carefully diluted with an equal volume of ethyl acetate, washed with saturated sodium bicarbonate, water, and saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure to give an brown oil. Purification by flash column chromatography (silica, 1-10% ether/hexanes) gave the desired 7-bromo-1-butylisoquinoline (1.50 g): ESI MS m/z 264 [M+H]+.

Quelle