Reacción #438718

Ecuación de reacción

ethyl 4-bromobenzoate

(4-n-pentyloxyphenyl)acetylene

→

ethyl 4-(4-n-pentyloxyphenylethynyl)benzoate

Rendimiento 35.2%

Disolventes

triethylamine

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling
2. 2
   Filtraciónthe precipitate was filtered off
3. 3
   Otrothe filtrate was evaporated under reduced pressure
4. 4
   Lavadothe solution was washed successively with 1N HCl, water, brine
5. 5
   Secadodried over magnesium sulfate
6. 6
   OtroThe solvents were removed under reduced pressure
7. 7
   Otrothe residue was triturated with acetonitrile
8. 8
   Filtracióncollected by filtration
9. 9
   Otrodried under reduced pressure

Procedimiento

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).

Fuente