Triethylamine → HCID 16050020, compound

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Reaction Steps

A mixture of methyl 2-bromo-5-nitrobenzoate (10 g) phenyl acetylene (4.2 ml), triethylamine (100 ml), cuprous iodide(0.4 g),dimethylformamide (200 ml) and bis-(triphenylphosphine)-palladium(II)chloride (1.35 g) was stirred at ambient temperature for 1 hour under an argon atmosphere. The solvents were removed under reduced pressure and the residue treated with 1N, hydrochloric acid (2 L) and then extracted with ethyl acetate (2×300 ml). The combined organic extracts were washed with saturated aequeous sodium bicarbonate solution (100 ml), water (3×100 ml) and brine (100 ml) filtered through phase separating paper and evaporated to dryness. The residue was purified by flash column chromatography on silica using ethyl acetate/hexane(gradient: 0 to 10%) as eluant to give methyl 2-(2-phenylethynyl)-5-nitrobenzoate (compound 76) as a yellow solid (9.98 g).

Provenance & Evidence