1,10-Dibromodecane → 1-Bromohexadec-1-yne

Participants

Reaction Steps

A 3 liter, 2-necked round bottom flask was equipped with a magnetic stir bar, an inlet valve and a septum. After being purged with an argon atmosphere, the flask was charged with 615 g (2.1 mol) of 1,10-dibromodecane in 350 mL of THF and 125 mL of hexamethylphosphorus triamide. A solution containing about 1 mol of hexynyllithium, prepared as described above, was then added to the solution of dibromide via the septum. The reaction mixture was allowed to stir overnight, then quenched by pouring over about 1 L of water. The reaction mixture was diluted with about 500 mL of hexane, phases separated and the organic layer washed twice with 500 mL aliquots of water. The organic layer was then dried over MgSO4, filtered, solvent stripped on the rotary evaporator, then vacuum distilled through a 2 foot column packed with 1/4" glass helices. About 104 g (35 mol % yield) of hexadecynyl bromide was obtained with a boiling point of 135° C. @ 0.3 mm Hg.

Provenance & Evidence