Benzyl Bromide → 1-(benzyloxy)pyridin-2(1H)-one

Participants

Reaction Steps

2-hydroxypyridine-1-oxide (0.50 g, 4.5 mmol) was reacted with benzyl bromide (0.64 mL, 5.4 mmol) in DMF (10 mL) in the presence of K2CO3 (1.8 g, 13.5 mmol) at 80° C. for 16 h. After cooling to room temperature, the solvent was removed by rotary evaporation. The crude product was redissolved in DCM and washed twice with water. The organic layer was then dried over MgSO4, filtered, and concentrated resulting in 7 as a white solid in 84% yield (0.78 g, 3.8 mmol) without the need for further purification. 1H NMR (400 MHz, CDCl3) δ=7.41-7.36 (m, 5H), 7.25 (td, J1=6.8 Hz, J2=2.0 Hz, 1H), 7.10 (dd, J1=7.2 Hz, J2=2.0 Hz, 1H), 6.68 (dd, J1=9.2 Hz, J2=1.6 Hz, 1H), 5.91 (td, J1=6.8 Hz, J2=1.6 Hz, 1H), 5.28 (s, 2H). 13C NMR (100 MHz, CDCl3) δ=159.2, 138.9, 136.9, 133.9, 130.3, 129.6, 128.9, 122.9, 104.7, 78.6. ESI-MS(+): m/z 202.19 [M+H]+, 224.29 [M+Na]+.

Provenance & Evidence