Water → HCID 68737131, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-bromo-4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-benzoic acid methyl ester (Example I13) (2.52 g) in dry N,N-dimethylformamide (75 ml) was added copper(I) cyanide (1.145 g). The reaction mixture was stirred at 160° C. for 40 minutes. The reaction mixture was allowed to cool to ambient temperature and was poured into a mixture of aqueous sodium carbonate (saturated) and water (1:2) (150 ml). The mixture was extracted with ethyl acetate (3×70 ml). The combined organic extracts were washed with water (2×70 ml) and brine (70 ml), dried over sodium sulfate and concentrated. The residue was re-crystallized from a mixture of diethyl ether and heptane (1:1) to give methyl 2-cyano-4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-benzoic acid methyl ester (1.474 g). 1H-NMR (CDCl3, 400 MHz): 8.23-7.45 (m, 6H), 4.11 (d, 1H), 4.03 (s, 3H), 3.74 (d, 1H).

Provenance & Evidence