Sodium hydride → 3-Bromo-4-(cyclopropylmethoxy)pyridine

Participants

Reaction Steps

To a solution of 3-bromo-4-chloropyridine (CAN 36953-42-1, 8 g, 41.6 mmol) in dry DMF (100 ml) under argon atmosphere at room temperature were added cyclopropylmethanol (CAN 2516-33-8, 3.15 g, 3.45 ml, 43.6 mmol) and by portions sodium hydride 60% (1.75 g, 43.6 mmol). The resulting reaction was stirred at room temperature until gas evolution stopped. The reaction mixture was then stirred at 100° C. for 3 hours, cooled down to room temperature and quenched by addition of water. The reaction mixture was concentrated in vacuo. The residue was dissolved in ethylacetate and extracted with an aqueous solution 1.0M sodium bicarbonate. The organic phase was collected, dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a heptane/ethylacetate gradient to yield the title compound (8.25 g, 87%) as a light yellow oil. MS (ESI, m/z): 228.2 (M+H+).

Provenance & Evidence