Methanol → HCID 67516356, compound

Participants

Reaction Steps

A mixture of (3-bromo-4-methylphenyl)(3,3-dimethyloxiran-2-yl)methanone (500 mg, 1.85 mmol, 1.0 eq) and hydroxylamine hydrochloride (500 mg, 7.19 mmol, 3.9 eq) in a 5:3 volumetric mixture of methanol and pyridine was heated at gentle reflux for 12 h. The resulting mixture was cooled to room temperature and the solvent was evaporated under vacuum. The residue was taken in water (10 mL) acidified with glacial acetic acid and stirred for 10 min. Ethyl acetate (50 mL) was added to the above mixture and the layers were separated. The aqueous layer was extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with water (20 mL), brine (20 mL), dried (Na2SO4) and filtered. The filtrate was evaporated under vacuum to afford 320 mg of the desired product as a white solid. 1HNMR (400 MHz, CDCl3) δ 7.97 (d, J=1.0 Hz, 1H), 7.65 (dd, J=1.0, 8.0 Hz, 1H), 7.26 (d, J=8.0 Hz, 1H), 4.78 (s, 1H), 2.42 (s, 3H), 1.51 (s, 3H), 1.31 (s, 3H); ESI-MS (m/z) 284, 286 [(MH)+, Br79,81].

Provenance & Evidence