Hexane → HCID 11735574, compound

Participants

Reaction Steps

2-Bromo-1,3-thiazole (2.0 g, 12 mmol) and CuI (460 mg, 2.4 mmol) were combined in DME (40 mL), and argon gas was bubbled through the suspension for several minutes to deoxygenate the mixture. Triethylamine (8.6 mL, 62 mmol) and PdCl2(PPh3)2 (856 mg, 1.22 mmol) were added and then phenylacetylene (3.7g, 36.5 mmol) was added dropwise. The reaction was heated to reflux at which point the reaction mixture solidified. Additional DME (20 mL) was added to dissolve the solids and the reaction mixture was allowed to stir for 16 h at reflux, at which time GC/MS showed no remaining 2-bromothiazole. After cooling, the mixture was diluted with 200 mL ethyl acetate, and filtered through Celite™. The pad was then washed thoroughly with ethyl acetate and the combined filtrates were washed with water (200 mL), brine (200 mL), dried over Na2SO4, and filtered. The filtrate was concentrated in vacuo, and the residue was purified by column chromatography eluting with hexane, then 97:3 hexane:ethyl acetate) to afford 2-(phenylethynyl)-1,3-thiazole (1.3 g, 60% yield) as a yellowish oil. 1H NMR (CDCl3, 300 MHz) δ 7.86 (d, J=3.2 Hz, 1H), 7.61–7.57 (m, 2H), 7.42–7.26 (m, 4H). MS (ESI) 185.2 (M+).

Provenance & Evidence