2,2'-Bipyridine → Bipyridine, polymer-bound

A solution of phenyllithium.cyclohexane/diethyl ether (40.9 ml, 38.4 mmol) was dropwise added to a mixture of 2,2′-bipyridine (5.0 g, 32.0 mmol) and diethyl ether (50 ml) at 5° C. while 15 minutes. This reaction mixture was stirred at room temperature for 2 hours, then the mixture was poured into water, an organic layer was separated from the mixture, furthermore an aqueous layer was extracted with dichloromethane. The organic layer was combined, and the solvent was distilled off, and the residue was diluted with acetone (50 ml), then saturated potassium permanganate acetone solution (120 ml) was added thereto, the mixture was stirred at room temperature for 1 hour. The obtained reaction mixture was filtered by Celite, the solvent of the filtrate was distilled off, and the residue was purified by silica gel column chromatography and recrystallization, thereby obtaining 4.2 g of 6-phenyl-2,2′-bipyridine as white crystal. Yield: 55.4%.

1. customan organic layer was separated from the mixture
2. extractionfurthermore an aqueous layer was extracted with dichloromethane
3. distillationthe solvent was distilled off
4. additionthe residue was diluted with acetone (50 ml)
5. additionsaturated potassium permanganate acetone solution (120 ml) was added
6. stirringthe mixture was stirred at room temperature for 1 hour
7. customThe obtained reaction mixture
8. filtrationwas filtered by Celite
9. distillationthe solvent of the filtrate was distilled off
10. customthe residue was purified by silica gel column chromatography and recrystallization

ORD record

ord-7964872ef94b4462aa6cb83eb4999bbc

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07442797B2