Reacción #2348100

Ecuación de reacción

4-pentylphenylboric acid

potassium carbonate

compound ( 21 )

3-iodo-4,5-difluorotoluene

→

3,4-difluoro-5-(4-pentylphenyl)toluene

Rendimiento 99.0%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaunder refluxing
2. 2
   Temperaturaby heating for 4 hours
3. 3
   OtroAfter removing Pd/C
4. 4
   Filtraciónby filtration
5. 5
   Otrothe filtrate was separated
6. 6
   Extracciónthe aqueous layer as extracted with toluene, which
7. 7
   workup.ADDITIONwas added to the organic layer
8. 8
   LavadoThe organic layer was washed with a saturated potassium hydrogensulfite aqueous solution and saturated saline
9. 9
   Secadodried over anhydrous magnesium sulfate
10. 10
    workup.DISTILLATIONThe solvent was distilled off
11. 11
    Otrothe residue was purified by silica gel column chromatography

Procedimiento

5.74 g of TBAB, 9.84 g of potassium carbonate and 0.76 g of Pd/C were added to 9.04 g of the compound (21) having been dissolved in a mixed solvent of 50 mL of toluene and 50 mL of Solmix, and 6.84 g of 4-pentylphenylboric acid, followed by stirring under refluxing by heating for 4 hours. After removing Pd/C by filtration, the filtrate was separated, and the aqueous layer as extracted with toluene, which was added to the organic layer. The organic layer was washed with a saturated potassium hydrogensulfite aqueous solution and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography to obtain 8.93 g of 3,4-difluoro-5-(4-pentylphenyl)toluene (22).

Fuente