Potassium Carbonate → 1-Bromo-3-ethynylbenzene

Participants

Reaction Steps

To each of two 1 L flasks was charged K2CO3 (68 g, 493.7 mmol), a large magnetic stirbar, and MeOH (250 mL). Stirring was begun and once the reaction mixtures were stirring without any problems, ((3-bromophenyl)ethynyl)trimethylsilane (12.5 g, 49.4 mmol, 10.5 mL) was added to each reaction vessel and the reaction mixtures were refluxed overnight. The cooled reaction mixtures were filtered and the filter cake was washed with MeOH. The filtrate was diluted with water and washed with Hexanes (at least 500 mL) three times. The combined organic layers were concentrated to give a yellow oil that was absorbed onto 50 g Celite. Flash chromatography (SiO2, Hexanes) provided 9.1 g, 50%, of the title compound as a colorless to light yellow oil.

Provenance & Evidence