Hydrochloric Acid → 3-Bromo-5-cyclopenten-1-ylpyridine

Participants

Reaction Steps

A solution of 1-(5-bromopyridin-3-yl)cyclopentanol (8) (1.7 g, 11.3 mmol) in 50 ml of toluene containing 5 ml of concentrated hydrochloric acid is heated at 120° C. for 12 hours with continuous carrying away of the water formed. The mixture is then poured into a saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The combined organic phases are washed with water and then with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue is purified by flash chromatography on silica gel (cyclohexane/ethyl acetate: 60/40). The title product is obtained in the form of a beige solid (1.65 g).

Provenance & Evidence