Réaction #2348100

Équation de réaction

4-pentylphenylboric acid

potassium carbonate

compound ( 21 )

3-iodo-4,5-difluorotoluene

→

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

Rendement 99.0%

Solvants

toluene

Conditions de réaction

Traitement

1. 1
   Températureunder refluxing
2. 2
   Températureby heating for 4 hours
3. 3
   AutreAfter removing Pd/C
4. 4
   Filtrationby filtration
5. 5
   Autrethe filtrate was separated
6. 6
   Extractionthe aqueous layer as extracted with toluene, which
7. 7
   workup.ADDITIONwas added to the organic layer
8. 8
   LavageThe organic layer was washed with a saturated potassium hydrogensulfite aqueous solution and saturated saline
9. 9
   Séchagedried over anhydrous magnesium sulfate
10. 10
    workup.DISTILLATIONThe solvent was distilled off
11. 11
    Autrethe residue was purified by silica gel column chromatography

Mode opératoire

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).

Source