Potassium Carbonate → 2-[2-(2,4'-Difluorobiphenyl-4-yl)ethyl]naphthalene

A mixture of 7.00 g (=18.61 mmol) of the above 2-[2-(3-fluoro-4-iodophenyl)ethyl]naphthalene, 3.12 g (=22.30 mmol) of 4-fluorophenylboric acid, 3.86 g (=27.93 mmol) of K2CO3, 1.50 g (=4.65 mmol) of tetrabutylammonium bromide, 0.39 g (=0.56 mmol) of dichlorobis(triphenylphosphine)palladium(II), 0.30 g (1.12 mmol) of triphenylphosphine and 60 ml of a mixed solvent of toluene/water/ethanol in a ratio of 1:1:1 was stirred for 4 hours with reflux. The reaction mixture obtained was extracted thrice with toluene, and then the extract was washed thrice with water and dried with anhydrous MgSO4. After the solvent was evaporated under a reduced pressure, the obtained orange solid of 8.48 g was purified with silica gel chromatography using heptane/toluene in a ratio of 5:1 as the eluent to obtain a white solid of 7.37 g, which was further recrystallized using a mixed solvent of Solumix/heptane in a ratio of 1:1 to obtain the target compound in an amount of 5.02 g. The product was characterized as the target compound based on results of various instrumental analyses, and the phase transition of the product is notated as “C 108.1 I”.

1. temperaturewith reflux
2. customThe reaction mixture obtained
3. extractionwas extracted thrice with toluene
4. washthe extract was washed thrice with water
5. dry with materialdried with anhydrous MgSO4
6. customAfter the solvent was evaporated under a reduced pressure
7. customthe obtained orange solid of 8.48 g was purified with silica gel chromatography
8. customto obtain a white solid of 7.37 g, which
9. customwas further recrystallized
10. customto obtain the target compound in an amount of 5.02 g
11. customon results of various instrumental analyses

ORD-Eintrag

ord-a70c005585534082a5b23b7877cddb72

Quelldatensatz

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07790915B2