Phenylacetylene → (Bromoethynyl)benzene

Participants

Reaction Steps

To a solution of sodium hypobromite [prepared by slow addition of bromine (11 ml) to 10M sodium hydroxide solution (50 ml) and crushed ice (100 g)] was added a solution of phenylacetylene (20.4 g, 19.97 mmol) in THF (10 ml). The two phase mixture was stirred vigorously for 5 hours. Saturated aq. ammonium chloride was added and the mixture was extracted with diethyl ether (3×30 ml). The combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was removed under reduced pressure to provide 1-bromo-2-phenyl-acetylene (36.2 g, 99%) as a yellow oil. 1H-NMR; δ (CDCl3), 7.50 (m). IR: Vmax (neat) 2200 cm-1.

Provenance & Evidence