2,2'-Bithiophene → 2-(5-Fluoro-2-thienyl)thiophene

Temperature

0 °C

2,2′-Bithiophene (7.40 g) in tetrahydrofuran (90 ml) was cooled to −78° C. under argon atmosphere, and thereto were added dropwise n-butyl lithium (1.59 M hexane solution, 28.0 ml). The mixture was stirred at 0° C. for one 30 minutes, and cooled again to −78° C. Added thereto was N-fluorobenzenesulfonimide (15.5 g), and the mixture was gradually warmed, and stirred at room temperature for 17 hours. The reaction mixture was poured into ice-cold water, and the solution was extracted with hexane twice, and the extract was washed successively with water and brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (hexane) to give 2-(5-fluoro-2-thienyl)thiophene (5.89 g) as colorless oil.

1. temperaturecooled again to −78° C
2. additionAdded
3. temperaturethe mixture was gradually warmed
4. stirringstirred at room temperature for 17 hours
5. additionThe reaction mixture was poured into ice-cold water
6. extractionthe solution was extracted with hexane twice
7. washthe extract was washed successively with water and brine
8. dry with materialdried over sodium sulfate
9. customThe solvent was evaporated under reduced pressure
10. customthe residue was purified by silica gel column chromatography (hexane)

ORD record

ord-dbb94eec81cf4ef8a309248b7be99187

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08222219B2