Dimethylformamide → 4-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl]-2-methylbenzonitrile

Participants

Reaction Conditions

Reaction Steps

Zinc(II) cyanide (0.47 g) was added at ambient temperature to a solution of 3-(4-bromo-3-methyl-phenyl)-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole (3.0 g) (Example I4) in N,N-dimethylformamide (80 ml). Under an atmosphere of argon, tetrakis(triphenylphosphine) palladium(0) (0.46 g) was added. The mixture was heated to 115° C. for 27 hours. The reaction mixture was cooled to ambient temperature, diluted with toluene, washed with aqueous ammonium hydroxide (1M), then with brine, dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 4:1) to give 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzonitrile (2.26 g) as a white solid. 1H-NMR (CDCl3, 400 MHz): 7.65 (t, 2H), 7.57 (d, 1H), 7.5 (s, 1H), 7.42 (m, 2H), 4.08 (d, 1H), 3.7 (d, 1H), 2.58 (s, 3H) ppm.

Provenance & Evidence