Triethylamine → ((2-Fluoro-5-nitrophenyl)ethynyl)trimethylsilane

Participants

Reaction Steps

To a solution of 3-bromo-4-fluoronitrobenzene (2 g, 9.1 mmol) in tetrahydrofuran (30 ml) was added triethylamine (1.9 ml, 13.6 mmol), trimethylsilylacetylene (1.9 ml, 13.6 mmol), triphenylphosphine (60 mg, 0.23 mmol) and dichlorobis(triphenylphosphine)palladium(II) (319 mg, 0.46 mmol). After stirring at room temperature for 20 minutes copper(I) iodide (17 mg, 0.09 mmol) was added and the mixture left to stir for 18 h at room temperature. The reaction mixture was quenched into isohexane (150 ml) and filtered through a plug of silica using isohexane as eluent. The solvent was removed in vacuo to leave (2-fluoro-5-nitrophenylethynyl)trimethylsilane as a brown solid: 1H NMR (360 MHz, CDCl3) δ 0.10 (9H, s), 7.02 (1H, dd, J 8, 1 Hz), 7.97-8.02 (1H, m), 8.17 (1H, dd, J 6, 3 Hz).

Provenance & Evidence