Hydrochloric Acid → HCID 53859083, compound

Participants

Reaction Steps

A solution of 4-(3-bromo-4-methoxyphenyl)-5-methoxy-3-methyl-4,5-dihydroisoxazole (260 mg, 0.87 mmol) in 15 mL of a 5:1 mixture of ethanol and 12N aqueous HCl was heated at reflux overnight. After cooling to room temperature, the reaction was concentrated to a small volume in vacuo. Saturated aqueous sodium bicarbonate (50 mL) was added and the mixture was extracted with 3×50 mL of ethyl acetate. The combined ethyl acetate layers were washed with 50 mL of brine, dried over sodium sulfate, and evaporated. The crude residue was subjected to flash chromatography on 25 g of silica gel eluting with 500 mL of 20% of diethyl ether/hexane to give 4-(3-bromo-4-methoxyphenyl)-3-methylisoxazole (158 mg, 68% yield) as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.40 (s, 1H), 7.57 (d, 1H, J=2 Hz), 7.29 (dd, 1H, J=9, 2 Hz), 6.86 (d, 1H, J=9 Hz), 3.94 (s, 3H), 2.40 (s, 3H). Mass spectrum (ESI): m/e=268 (M+1).

Provenance & Evidence