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

Participants

Reaction Steps

To a solution of 3-bromo-4-chloropyridine (CAN 36953-42-1, 5 g, 26.0 mmol) in dry DMF (60 ml) under an argon atmosphere at room temperature was added cyclopropylmethanol (CAN 2516-33-8, 1.97 g, 27.3 mmol) and sodium hydride 60% (1.09 g, 27.3 mmol) by portions. The resulting reaction was stirred at room temperature until gas evolution stopped. The reaction mixture was then stirred at 100° C. for 3 h. The reaction was cooled down to room temperature, quenched by addition of water and the reaction mixture was concentrated in vacuo. The residue was dissolved in ethylacetate, extracted with 1.0M aqueous solution sodium bicarbonate, organic phase dried over sodium sulfate and evaporated down to dryness. The crude was purified by flash chromatography on silica eluting with a heptane/ethylacetate gradient to yield the titled compound (5.8 gr, 98%) as a light yellow oil. MS (ESI, m/z): 228.1 (M+H+).

Provenance & Evidence