Reaktion #52338

Reaktionsgleichung

ethyl-2-fluoro-4-trifluoromethylsulfonyloxy-benzoate

Intermediate 6

ethyl-2-fluoro-4-trifluoromethylsulfonyloxy-benzoate

(trimethylsilyl)acetylene

→

title compound

Ausbeute 94.6%

Ethyl-2-fluoro-4-trimethylsilanylethynyl-benzoate

Ausbeute 94.6%

Lösungsmittel

diethyl ether

triethyl amine

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigesparged with argon
2. 2
   Sonstigethe resulting reaction mixture
3. 3
   TemperaturIt was then cooled to ambient temperature
4. 4
   Filtrationfiltered over a bed of celite
5. 5
   SonstigeThe filtrate was evaporated in vacuo to an oil which

Vorschrift

A solution of ethyl-2-fluoro-4-trifluoromethylsulfonyloxy-benzoate (Intermediate 6, 1.82 g, 6 mmol) in triethyl amine (12 mL) and anhydrous tetrahydrofuran (30 mL) was treated with copper(I)iodide (0.12 g, 0.6 mmol) and sparged with argon. Dichlorobis(triphenylphosphine)palladium(II) (0.43 g, 0.6 mmol) was added followed by (trimethylsilyl)acetylene (3.6 mL, 24 mmol) and the resulting reaction mixture was heated at 70° C. overnight. It was then cooled to ambient temperature, diluted with diethyl ether and filtered over a bed of celite. The filtrate was evaporated in vacuo to an oil which was subjected to flash column chromatography over silica gel (230-400 mesh) using 5% ethyl acetate in hexane as the eluent to afford the title compound as an orange oil (1.5 g, quantitative).

Quelle