Reaktion #438718

Reaktionsgleichung

ethyl 4-bromobenzoate

(4-n-pentyloxyphenyl)acetylene

→

ethyl 4-(4-n-pentyloxyphenylethynyl)benzoate

Ausbeute 35.2%

Lösungsmittel

triethylamine

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Filtrationthe precipitate was filtered off
3. 3
   Sonstigethe filtrate was evaporated under reduced pressure
4. 4
   Waschenthe solution was washed successively with 1N HCl, water, brine
5. 5
   Trocknendried over magnesium sulfate
6. 6
   SonstigeThe solvents were removed under reduced pressure
7. 7
   Sonstigethe residue was triturated with acetonitrile
8. 8
   Filtrationcollected by filtration
9. 9
   Sonstigedried under reduced pressure

Vorschrift

To a suspension of ethyl 4-bromobenzoate (1.37 g), (4-n-pentyloxyphenyl)acetylene (565 mg), triphenylphosphine (16 mg) and copper(I) iodide (6 mg) in triethylamine (10 ml) and pyridine (4 ml) was added palladium(II) chloride bis(triphenylphosphine) (21 mg) and the reaction mixture was stirred for 24 hours at 80° C. After cooling, the precipitate was filtered off, and the filtrate was evaporated under reduced pressure. The residue was taken up to dichloromethane, and the solution was washed successively with 1N HCl, water, brine and dried over magnesium sulfate. The solvents were removed under reduced pressure and the residue was triturated with acetonitrile, collected by filtration and dried under reduced pressure to give ethyl 4-(4-n-pentyloxyphenylethynyl)benzoate (355 mg).

Quelle