Potassium Carbonate → HCID 71138918, compound

Participants

Reaction Steps

To a stirring reaction mixture of 3-methoxypyridine-2-one (2.00 g, 16 mmol) and K2CO3 (4.42 g, 32 mmol) in THF was added 4-bromobenzyl bromide (5.20 g, 20.8 mmol) slowly. Reaction mixture was the heated to reflux and stirring continued overnight. Reaction mixture was then cooled down and separated into organic and aqueous layer by adding CH2Cl2 (120 mL) and water (60 mL). Organic layer was separated and subsequently washed with water (2×60 mL), brine (1×40 mL). Organic layer was dried on Na2SO4 and solvent was evaporated in vacuo. Crude yellowish solid was triturated with hexanes to give pure white solid 145 (3.49 g, 74%) without further purification. 1H NMR (400 MHz, CDCl3) δ 7.25 (m, 2H), 7.04 (m, 2H), 6.78 (dd, J=6.8, 1.2 Hz, 1H), 6.45 (dd, J=7.2, 1.6 Hz, 1H), 5.94 (t, J=7.2 Hz, 1H), 4.95 (s, 2H), 3.64 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 157.71, 149.91, 135.29, 131.49, 129.59, 127.53, 121.57, 111.82, 104.98, 55.54, 51.10. HRMS (EI) calcd for C13H12BrNO2 [M]+ 293.0051. found 293.0051.

Provenance & Evidence