Benzyl Bromide → HCID 178517714, compound

Participants

Reaction Steps

To a stirred solution of potassium hydroxide (2.52 g, 45.00 mmol) in methanol (30 mL), was added pyridine-2,3-diol (5.00 g, 45.0 mmol) in 3 portions and a clear red solution was obtained. To this clear red solution was added benzyl bromide (7.70 g, 5.35 mL, 45.00 mmol). The reaction mixture was kept stirring at ambient temperature for 30 minutes, then at 40° C. for 2 hours. The solvent was removed in vacuo and the residue was dissolved in dichloromethane (100 mL), and washed with water (100 mL). The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo. The residue was recrystallized from methanol (20 mL) to afford the title compound (4.60 g, 51%): 1H NMR (300 MHz, DMSO-d6) δ 11.63 (s, 1H), 7.44-7.33 (m, 5H), 6.96-6.88 (m, 2H), 6.07 (t, J=6.0 Hz, 1H), 5.00 (s, 2H); MS (ES+) m/z 202.2 (M+1).

Provenance & Evidence