Water → 5-(Benzyloxy)-2-fluoropyridine

Participants

Reaction Steps

A solution of 2-fluoro-5-hydroxypyridine (Combi-block) (1.00 g, 8.84 mmol) in DMF (12 mL) was treated with sodium hydride, 60% dispersion in mineral oil (Alfa-Aesar) (0.88 g, 22.1 mmol) at rt under N2. After stirring for 40 min, benzyl chloride (Aldrich) (3.05 mL, 26.5 mmol) and tetrabutylammonium iodide (Aldrich) (0.33 g, 0.88 mmol) were added, and the reaction mixture was stirred for a further 2 h. Water (2 mL) was added to quench the reaction, and the reaction mixture was partitioned between EtOAc and sat. NaHCO3. The aqueous layer was extracted with EtOAc (2×15 mL). The combined organic extracts were washed with sat. NaHCO3, brine, dried over MgSO4 and concentrated. The residue was purified by column chromatography (120 g, 10% to 20% actone in hexanes) to give the product as a colorless liquid (1.32 g). m/z (ESI, +ve ion) 204.0 (M+H)+. 1H NMR (300 MHz, CDCl3) δ 7.91 (br. s., 1H); 7.32-7.51 (m, 6H); 6.86 (dd, J=8.84, 3.29 Hz, 1H); 5.10 (s, 2H).

Provenance & Evidence