Phosphorus tribromide → (E,E)-1-bromo-2,4-pentadecadien-6,9-diyne

Participants

Reaction Steps

A solution of (E)-1,4-pentadecadien-6,9-diyn-3-ol (8.5 g) in ether (200 mL) was cooled to -40° and treated over 5 min with phosphorous tribromide (3.7 mL) dissolved in ether (70 mL). The cooling bath was removed and the reaction mixture was warmed to 0° over 1 hour and then poured onto ice. The ether extract was then washed with water, sodium carbonate solution (10 mL) and dried (MgSO4). Removal of the solvents and purification of the residue by liquid chromatography (two columns, hexane) gave (E,E)-1-bromo-2,4-pentadecadien-6,9-diyne as pure material (7.8 g).

Provenance & Evidence