Ethyl bromoacetate → Ethyl 3-(3,5-bis(trifluoromethyl)phenyl)-3-cyanopropanoate

Participants

Reaction Conditions

Reaction Steps

A solution of 3,5-bis(trifluoromethyl)phenylacetonitrile (8.30 g) in tetrahydrofuran (80 ml) was cooled to −78° C. under an argon gas atmosphere, and a solution (1.9 M, 17.3 ml) of sodium hexamethyldisilazane in tetrahydrofuran was added dropwise. After the completion of the dropwise addition, the solution was stirred at 10° C. for 15 min, and cooled to −78° C. again. To the solution was added ethyl bromoacetate (5.48 g), and the mixture was stirred at room temperature for 16 hr. The reaction solution was partitioned between ethyl acetate and water, and the ethyl acetate layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate 100:0-70:30) to give the title compound (7.50 g, yield 67%) as a brown oil.

Provenance & Evidence