3,4,5-TRIFLUOROPHENYLACETONITRILE

3, 4, 5-trifluorobenzylbromide (5.00 g, 22.2 mmol) (manufactured by Tokyo Kasei Kogyo Co., Ltd.) in acetonitrile (40 ml) solution in water (10 ml), potassium cyanide (1.74 g, 26.7 mmol) and 18-crown-6-ether (manufactured byTokyo Kasei Kogyo Co., Ltd.) and (0.590 g, 2.22 mmol) was added at roomtemperature and stirred for 3 hours at 50 ° C. To the reaction mixture waspoured into water and extracted with ethyl acetate. The extract was washed withsaturated brine, dried over anhydrous sodium sulfate, and concentrated underreduced pressure. The concentrate was purified by silica gel columnchromatography and purified by (elution solvent ethyl acetate / n-hexane = 1/3)to give a colorless oil (yield 3.74 g, 98percent yield). Sodium hydride indimethoxyethane solution (40ml) of the resulting oil (60percent, 2.19g, 54.6mmol) wasadded and methyl iodide (15.5g, 110mmol) at 0 ° C, 1 at room temperature timeand stirred. To the reaction mixture was poured into water and extracted withethyl acetate. The extract was washed with saturated brine, dried overanhydrous sodium sulfate, and concentrated under reduced pressure. Theconcentrate was purified by silica gel column chromatography and purified by(elution solvent ethyl acetate / n-hexane = 1/5) to give a white solid (Yield4.00 g, 92percent yield). Obtained after stirring for 2 h with acetic acid solution(20ml) in 60percent aqueous sulfuric acid (40 ml) was added 120. ° C solid sodiumnitrite (6.90 g, 100 mmol) was added at room temperature, 2 in 90 ° C time and stirred.After washing the reaction mixture was poured ice water the precipitated solidwith water to give a white solid (Yield 3.86 g, 87percent yield) by vacuum drying. Tothe resulting solid in dichloromethane (40 ml) oxalyl chloride (3.36g, 26.5mmol) and N, was added N- Dimethylformamide (0.10 mmol), and refluxed for 1hour. The reaction solution was concentrated under reduced pressure, to give ayellow solid (4.63g). The resulting solid in tetrahydrofuran (40 ml) lithiumaluminum hydride (686mg, 18.1mmol) was added at 0 ° C, and stirred at roomtemperature for 1 hour. To the reaction mixture was poured into diethyl etherand stirred for 1 hour at room temperature was added a small amount of water.Except for the precipitate by suction filtration, dried over anhydrous sodiumsulfate, and concentrated under reduced pressure. The concentrate was purifiedby silica gel column chromatography and purified by (elution solvent ethylacetate / n-hexane = 1/3) to give the title compound as a colorless oil (yield3.13 g, 87percent yield).

Molecular Weight:171.12
XLogP3:1.9
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:171.02958362
Monoisotopic Mass:171.02958362
Topological Polar Surface Area:23.8
Heavy Atom Count:12
Complexity:186
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes