Reaktion #90089

Reaktionsgleichung

hydrochloric acid

methanesulfonic acid

2-(3-bromo-4-methoxy-phenyl)-2-methyl-propionitrile

bromoethyl acetate

→

title compound

Ausbeute 72.0%

4-(3-Bromo-4-methoxy-phenyl)-4-methyl-3-oxo-pentanoic acid ethyl ester

Ausbeute 72.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGThe mixture was further stirred for 30 min
3. 3
   workup.STIRRINGstirred at room temperature overnight
4. 4
   ExtraktionAfter extraction with ethyl acetate
5. 5
   Waschenthe organic layer was washed with brine
6. 6
   Trocknendried over sodium sulfate
7. 7
   SonstigeThe drying agent was removed by filtration
8. 8
   Sonstigethe residues obtained
9. 9
   Einengenafter concentration under reduced pressure
10. 10
    Sonstigewere purified by silica gel column chromatography (ethyl acetate/hexane)

Vorschrift

To the THF suspension of zinc (5.72 g, 2 eq.), methanesulfonic acid (25.6 μl, 0.01 eq.) was added, and then stirred at 80° C. for 10 min. Then, the THF solution of 2-(3-bromo-4-methoxy-phenyl)-2-methyl-propionitrile (10 g, 39.35 mmol) was added, followed by addition of bromoethyl acetate (11.07 ml, 1.6 eq.) over 1 hr. The mixture was further stirred for 30 min. To the reaction solution, 4 M hydrochloric acid was added, and stirred at room temperature overnight. After extraction with ethyl acetate, the organic layer was washed with brine and dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (orange oily substance, 9.74 g, 72%).

Quelle