Reaction #2348100

Reaction equation

4-pentylphenylboric acid

potassium carbonate

compound ( 21 )

3-iodo-4,5-difluorotoluene

→

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

Yield 99.0%

Solvents

toluene

Conditions

Workup

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

Procedure

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