Triphenylphosphine → [2-(3-Methanesulfonylphenyl)ethynyl]trimethylsilane

Participants

Reaction Conditions

Reaction Steps

Into a sealable tube was weighed 2.06 g (8.76 mmol) of 1-bromo-3-methanesulfonyl-benzene, 93 mg of palladium acetate, 122 mg of triphenylphosphine, 79 mg of copper (I) iodide, 10.0 mL of triethylamine, and 2.0 mL of trimethylsilylacetylene. The reaction vessel was sealed and was heated at 80-85° C. for 1 h then was filtered of solids with added ethyl acetate. The filtrate was concentrated in vacuo and was purified by silica gel flash chromatography (Jones Flashmaster, 50 g Silica gel, gradient elution from 100% hexanes to 40% ethyl acetate over 30 minutes). Appropriate fractions were combined and concentrated in vacuo affording (3-methanesulfonyl-phenylethynyl)-trimethylsilane as a faintly yellow oil, yield: 1.60 g (72%). 1H NMR (CDCl3): δ 8.04 (s, 1H), 7.88 (d, J=8 Hz, 1H), 7.71 (d, J=8 Hz, 1H), 3.05 (s, 3H), 0.27 (s, 9H).

Provenance & Evidence