Boron tribromide → HCID 178518639, compound

Participants

Reaction Steps

A mixture of p-methoxyphenyl nitrone 128 (2 mmol) and BBr3 (1M in CH2Cl2, 15 mL, 15 mmol) in CH2Cl2 (100 mL) was stirred for 20 h, then evaporated. The residue was evaporated with MeOH (25 mL, repeated twice), then water (50 mL) was added. The reaction mixture was basified with saturated NaHCO3 to pH 8, stirred for 1 h and acidified with 2N HCl to pH 3. The precipitated crude product was filtered, washed with water to a neutral pH, air dried and recrystallized from EtOH to give the title compound. Yield: 71%; mp 276°-278° C. (from EtOH); IR (KBr) 3422, 3069, 1670, 1653, 1609, 1590, 1459, 1361, 1297 and 1226 cm-1 ; 1H NMR (in DMSO-d6) δ6.83 (d, 2H, J=8.7 Hz), 7.41 (s, 1H), 7.99 (s, 1H), 8.27 (d, 2H, J=8.7 Hz), 10.09 (br.s, 1H, O--H), 12.53 (br.s, 1H, N--H); HPLC: 98%; HRMS Calcd for C14H8N2O3Cl2 : 321.9912.

Provenance & Evidence