Hydrochloric Acid → 4-(5-(3,5-Dichlorophenyl)-5-(tri fluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid

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Reaction Conditions

Reaction Steps

Lithium hydroxide (51 mg) was added at ambient temperature to a solution of 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid ethyl ester (0.27 g) (Example I4) in tetrahydrofuran (3 ml) and water (0.75 ml). The reaction mixture was stirred at 50° C. for 18 hours. The reaction mixture was cooled to ambient temperature and diluted with water, acidified by addition of aqueous hydrochloric acid (2M) and extracted three times with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated to give 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid (0.25 g), which was used without further purification. 1H-NMR (DMSO-d6, 400 MHz): 13.1 (s, 1H), 7.90 (d, 1H), 7.80 (s, 1H), 7.65 (m, 4H), 4.40 (m, 2H), 2.55 (s, 3H).

Provenance & Evidence