Pyridine → 1-Bromo-2-octyne

Under argon atmosphere, anhydrous pyridine (0.4 ml, 4.9 mmol) was added to a solution of 2-octyne-1-ol (9.4658 g, 75.0 mmol) in anhydrous ether (50 ml). To the mixture was added dropwise phosphorus tribromide (2.35 ml, 25.0 mmol) at -30° to -35° C. and the mixture was stirred at the same temperature for one hour and then stirred for one hour at room temperature under argon atmosphere. To the resulting mixture was added brine (100 ml), and the mixture was then extracted with ether (50 ml×4). The combined ether layers were washed with an aqueous saturated solution of sodium bicarbonate (150 ml), with water (150 ml) and with brine (150 ml), dried over anhydrous sodium sulfate (40 g), and concentrated. Distillation of the residue gave a colorless oily product of 1-bromo-2-octyne (9.1493 g, 65%, B.p.: 53°-58° C./0.39 mmHg). The product was assigned the structure by the following data.

1. stirringstirred for one hour at room temperature under argon atmosphere
2. extractionthe mixture was then extracted with ether (50 ml×4)
3. washThe combined ether layers were washed with an aqueous saturated solution of sodium bicarbonate (150 ml), with water (150 ml) and with brine (150 ml)
4. dry with materialdried over anhydrous sodium sulfate (40 g)
5. concentrationconcentrated
6. distillationDistillation of the residue

ORD record

ord-dcbfc3cfc92642c48a22949a913dfc34

Source dataset

uspto-grants-1988_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04775692