Iodoethane → 3-Bromo-5-(ethoxymethyl)pyridine

Participants

Reaction Steps

To a mixture of powdered KOH (5.96 g, 106.4 mmol) in anhydrous DMSO (20 mL) was added under argon a solution of (5-bromopyridin-3-yl)methanol (example 26c) (5 g, 26.6 mmol) in anhydrous DMSO (20 mL), followed by EtI (2.6 mL, 31.9 mmol). The reaction mixture was stirred at room temperature for 1 hour then diluted with water and extracted with EtOAc. The organic phase was washed with water and brine, dried over MgSO4, filtered and evaporated to give 5.6 g of 3-bromo-5-(ethoxymethyl)pyridine as a dark brown oil in 97% yield. 1H NMR (400 MHz, CDCl3): 1.27 (t, 3H), 3.57-3.59 (q, 2H), 4.50 (s, 2H,), 8.48 (s, 1H), 8.60 (s, 1H).

Provenance & Evidence