Pyridine → 1-Bromo-2-octyne

Participants

Reaction Steps

Under argon atmosphere, anhydrous pyridine (0.4 ml, 4.9 mmol) was added to a solution of 2-octyne-1-ol (9.4658 g, 75 mmol) in anhydrous ether (50 ml). To the mixture, there was dropwise added phosphorus tribromide (2.35 ml, 25.0 mmol) at -30° C. to -35° C., and the resulting reaction mixture was stirred for one hour. The mixture was then stirred at room temperature for one hour. Brine (100 ml) was added to the reaction mixture followed by extraction with ether (50 ml×4). The organic layers were combined, washed with saturated aqueous sodium hydrogencarbonate solution (150 ml), with water (150 ml) and with brine (150 ml), and dried over anhydrous sodium sulfate (40 g) to concentrate. The residue was distilled (b.p.=53°-58° C. at 0.39 mmHg), yielding a colorless oil, 1-bromo-2-octyne (9.1493 g, 63% yield). The structure was confirmed by the following data.

Provenance & Evidence