Pyridine → 1-Bromo-2-octyne

A solution of 2-octyne-1-ol (37.8 g) in ether (150 mL) containing pyridine (3 ml) was cooled to -35° and treated with a solution of phosphorous tribromide (28.9 g) over 45 min. The mixture was then stirred at -30° for 2 hours, 3 hours at room temperature and 1/2 hour at 40°. The reaction mixture was then cooled to room temperature, poured onto ice and extracted with ether. The combined ether extracts were washed with aqueous NaHCO3 solution, brine and dried (MgSO4). Removal of the solvents and distillation of the residue yielded 1-bromo-2-octyne (40.9 g), bp, 106°-110° (25 mmHg).

1. temperaturewas cooled to -35°
2. temperatureThe reaction mixture was then cooled to room temperature
3. additionpoured onto ice
4. extractionextracted with ether
5. washThe combined ether extracts were washed with aqueous NaHCO3 solution, brine
6. dry with materialdried (MgSO4)
7. customRemoval of the solvents and distillation of the residue

ORD record

ord-74292a435e3b458a8a47ff14ea326f30

Source dataset

uspto-grants-1982_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04311645