1,2-difluoro-3-iodo-5-methylbenzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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 hydrogen sulfite 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). under refluxing by heating for 4 hours After removing Pd/C by filtration the filtrate was separated the aqueous layer as extracted with toluene, which was added to the organic layer The organic layer was washed with a saturated potassium hydrogen sulfite aqueous solution and saturated saline dried over anhydrous magnesium sulfate The solvent was distilled off the residue was purified by silica gel column chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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). under refluxing by heating for 4 hours After removing Pd/C by filtration the filtrate was separated 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 dried over anhydrous magnesium sulfate The solvent was distilled off the residue was purified by silica gel column chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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). under refluxing by heating for 4 hours After removing Pd/C by filtration the filtrate was separated 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 dried over anhydrous magnesium sulfate The solvent was distilled off the residue was purified by silica gel column chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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 hydrogen sulfite 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). under refluxing by heating for 4 hours After removing Pd/C by filtration the filtrate was separated the aqueous layer as extracted with toluene, which was added to the organic layer The organic layer was washed with a saturated potassium hydrogen sulfite aqueous solution and saturated saline dried over anhydrous magnesium sulfate The solvent was distilled off the residue was purified by silica gel column chromatography