Triphenylphosphine → (3-Chlorophenylethynyl)trimethylsilane

Chloro-3-iodobenzene (10.0 g, 41.9 mmol) was dissolved in 100 mL dry THF and 17.5 mL triethyl amine. This mixture was evacuated and backfilled with argon several times to remove oxygen from the solution. Triphenylphosphine (329 mg, 1.25 mmol) and bis(triphenylphosphine)palladium(II)chloride (1.47 g, 2.09 mmol) were added and the reaction mixture was stirred at room temperature for 1 h. Copper(I)iodide (239 mg, 1.25 mmol) and trimethylsilylacetylen (6.28 g, 6.39 mmol) were added. The reaction mixture was stirred at room temperature overnight. The solvent was evaporated. The residue was taken up in 500 mL water and extracted three times with ethyl acetate (500 mL each). The combined organic extracts were dried with magnesium sulfate, filtered and evaporated. The crude product was purified by flash-chromatography on silica gel (heptane/ethyl acetate 100:0->80:20 gradient). The desired product was obtained as a light yellow oil (7.38 g, purity ˜70%, yield ˜59%).

1. customThis mixture was evacuated
2. customto remove oxygen from the solution
3. stirringThe reaction mixture was stirred at room temperature overnight
4. customThe solvent was evaporated
5. extractionextracted three times with ethyl acetate (500 mL each)
6. dry with materialThe combined organic extracts were dried with magnesium sulfate
7. filtrationfiltered
8. customevaporated
9. customThe crude product was purified by flash-chromatography on silica gel (heptane/ethyl acetate 100:0->80:20 gradient)

ORD record

ord-dc3c51ad74ee4933b2a0e2f3352beb2b

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07241760B2