Water → 7-Bromo-1-methyldibenz[b,f][1,4]oxazepine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-[(4-bromo-2-fluorophenyl)iminomethyl]-3-methylphenol (31.7 g, 102.9 mmol) in DMSO (0.27 L), K2CO3 (28.6 g, 206.9 mmol) and 18-Crown-6 (477 mg, 1.8 mmol) were added. The resulting mixture was stirred at 140° C. for 1 h and then allowed to cool to ambient temperature. Water was added and the mixture was extracted with toluene/ethyl acetate (8:2). The combined organic layers were washed with water and with brine, dried (Na2SO4) and evaporated to afford the crude compound which was purified by flash chromatography (SiO2, CH2Cl2) to give 7-bromo-1-methyldibenz[b,f][1,4]oxazepine (25.05 g, 84%). 1H-NMR (400 MHz, CDCl3) δ 2.47 (s, 3H), 7.01 (m, 2H), 7.18-7.37 (m, 4H), 8.77 (s, 1H). (m/z)=288+290 (M+H)+.

Provenance & Evidence