Benzyl Bromide → 2-(Benzyloxy)-4-ethoxy-5-iodopyridine

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-ethoxy-5-iodopyridin-2-ol (3.7 g, 13.96 mmol) in THF (10 mL) was added (bromomethyl)benzene (2.87 g, 16.75 mmol) and silver carbonate (7.70 g, 27.9 mmol). The mixture was stirred at 70° C. for 16 h. The reaction residue was then filtered and the filtrate was concentrated. The mixture was diluted with water (30 mL) and extracted with DCM (30 mL×2). The combined organic extract was washed with brine, dried over MgSO4, filtered and concentrated. The crude material was purified by silica column chromatography (PE/EA=5:1). All fractions found to contain product by TLC (PE/EA=5:1, Rf=0.6) were combined and concentrated to yield a light yellow oil of 2-(benzyloxy)-4-ethoxy-5-iodopyridine (4.2 g, 10.64 mmol, 76% yield). 1H NMR (400 MHz, MeOH-d4) δ 8.25 (s, 1H), 7.47-7.41 (m, 2H), 7.40-7.30 (m, 3H), 6.41 (s, 1H), 5.32 (s, 2H), 4.16 (q, J=7.2 Hz, 2H), 1.47 (t, J=7.2 Hz, 3H); ES-LCMS m/z 356.0 (M+H).

Provenance & Evidence