4-Methoxybenzyl alcohol → HCID 90415859, compound

Participants

Reaction Steps

To a mixture of (4-methoxyphenyl)methanol (16.71 g, 121 mmol) in DMF (300 mL) was added NaH (3.96 g, 165 mmol) at 0° C. dropwise. After the mixture was stirred for 30 min, 5-bromo-2-chloro-3-ethoxypyridine (26 g, 110 mmol) in DMF (100 mL) was added to above mixture and the mixture was stirred for 12 h at 80-90° C. The mixture was quenched by H2O (20 mL), extracted with DCM (400 mL×2), dried over Na2SO4, filtered, and concentrated to give the residue which was purified by column chromatography (10% EA: 90% PE, 360 g silica column). All fractions found to contain product by TLC (EA: PE=1:5, Rf=0.5) were combined and concentrated to yield a white solid of 5-bromo-3-ethoxy-2-((4-methoxybenzyl)oxy)pyridine (36 g, 74.5 mmol, 68% yield): 1H NMR (400 MHz, CD3OD) δ 7.71 (d, J=2.0 Hz, 1H), 7.36-7.31 (m, 3H), 6.89-6.87 (m, 2H), 5.27 (s, 2H), 4.05-4.00 (m, 2H) 3.77 (s, 3H), 2.37 (d, J=7.0 Hz, 3H); ES-LCMS m/z 338 (M+H).

Provenance & Evidence