Water → HCID 86049356, compound

Participants

Reaction Steps

To a solution of 2-bromo-4′-methyl-acetophenone (6.514 g, 27.5 mmol) in methanol at 50° C. was added water until the solution turned slightly cloudy. Methoxylamine hydrochloride (7.037, 85.7 mmol) was added and the mixture was stirred overnight. The solvent was removed under high vacuum and the residue was extracted with EtOAc and dried over MgSO4. The product was purified by flash chromatography on silicagel (CH2Cl2/hexanes) to give 2 isomers in 87% total yield: 2 isomers in 87% total yield: Z-isomer 1H NMR 500 MHz (DMSO-d6) δ 2.33 (s, 3H), 3.83 (s, 3H), 4.62 (s, 2H), 7.26 (dd, 2H, J=1.8, 8.2 Hz), 7.51 (d, 2H, J=7.6 Hz); FABHRMS: found M+, 242.0177 (calcd for C10H13ONBr: M+, 242.0175). E-isomer 1H-NMR 500 MHz (DMSO-d6) d 2.33 (s, 3H), 3.99 (s, 3H), 4.68 (s, 2H), 7.25 (d, 2H, J=8.2 Hz), 7.61 (d, 2H, J=7.3 Hz); FABHRMS: found M+, 242.0175 (calcd for C10H13ONBr: M+, 242.0175).

Provenance & Evidence