Water → 5-Bromo-2-[(oxolan-3-yl)oxy]pyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-2-fluoropyridine (1.5 mL, 14.2 mmol) in DMF (14 mL) was added Cs2CO3 (9.3 g, 28.5 mmol) and 3-hydroxytetrahydrofuran (1.7 mL, 21.3 mmol). The reaction mixture was heated at 90° C. for 3 days then allowed to cool to room temperature (rt). Water was added and product was filtered off, washed with water, and dried under vacuum overnight (3.5 g, 100%). MS (ESI): mass calcd. for C9H10BrNO2, 243.0; m/z found, 244.3, 246.3 [M+H]+. 1H NMR (CDCl3): 8.17 (d, J=2.1 Hz, 1H), 7.64 (dd, J=8.8, 2.6 Hz, 1H), 6.66 (dd, J=8.7, 0.5 Hz, 1H) 5.52-5.48 (m, 1H), 4.04-3.95 (m, 2H), 3.93-3.86 (m, 2H), 2.30-2.19 (m, 1H), 2.15-2.08 (m, 1H).

Provenance & Evidence