Reaktion #1607467

Reaktionsgleichung

acetic anhydride

methyl 4-((1-(4-bromo-2-methylphenyl)-4,4,4-trifluorobutyl)amino)benzoate

N,N-diisopropylethylamine

lithium acetate

→

title compound

Ausbeute 52.6%

3-methyl-4-(4,4,4-trifluoro-1-((4-(methoxycarbonyl)phenyl)amino)butyl)benzoic acid

Ausbeute 52.6%

Lösungsmittel

DMF

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthe insoluble material was filtered off through celite
2. 2
   ExtraktionThe filtrate was extracted with ethyl acetate
3. 3
   Waschenthe extract was washed with 1M hydrochloric acid and saturated brine
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   SonstigeThe solvent was evaporated under reduced pressure
6. 6
   Sonstigethe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Vorschrift

Under a nitrogen atmosphere, to a mixture of methyl 4-((1-(4-bromo-2-methylphenyl)-4,4,4-trifluorobutyl)amino)benzoate (racemate) (1.5 g), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.285 g), N,N-diisopropylethylamine (3.65 mL), lithium acetate 2 hydrate (2.85 g) and DMF (17 mL) was added acetic anhydride (1.977 mL), and the mixture was stirred at 120° C. overnight. To the reaction mixture was added water at room temperature, and the insoluble material was filtered off through celite. The filtrate was extracted with ethyl acetate, and the extract was washed with 1M hydrochloric acid and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (725.6 mg).

Quelle