Reaktion #2157543

Reaktionsgleichung

bromine

2′-(Trifluoromethyl)acetophenone

water

→

2-bromo-1-(2-trifluoromethylphenyl)ethanone

Lösungsmittel

diethyl ether

chloroform

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter the dropwise addition
2. 2
   Extraktionthe mixture was extracted with chloroform
3. 3
   WaschenThe extract was washed with saturated brine
4. 4
   Trocknendried over anhydrous magnesium sulfate, concentration under reduced pressure

Vorschrift

2′-(Trifluoromethyl)acetophenone (10.0 g) was dissolved in chloroform (30 mL) and diethyl ether (30 mL), a solution of bromine (8.50 g) in chloroform (20 mL) was added dropwise while maintaining the reaction temperature at not higher than 25° C. After the dropwise addition, the mixture was stirred at room temperature for 1 hr, water was added to the reaction mixture and the mixture was extracted with chloroform. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, concentration under reduced pressure to give crude 2-bromo-1-(2-trifluoromethylphenyl)ethanone. Potassium carbonate (13.82 g) was added to ethyl cyanoacetate (44.44 g), and the mixture was stirred at 45° C. for 1 hr. A solution of crude 2-bromo-1-(2-trifluoromethylphenyl)ethanone in acetone (100 mL) was added dropwise. After completion of the dropwise addition, the mixture was stirred at the same temperature for 1 hr, and stirred overnight at room temperature. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Excess ethyl cyanoacetate contained in the obtained oil was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→7:1) to give the title compound as an oil (yield 10.43 g, from 2′-(trifluoromethyl)acetophenone, yield 66%).

Quelle