Thiophene → HCID 19813480, compound

Temperature

-15 °C

To a solution of thiophene (4.2 g) in dry tetrahydrofuran (25 ml) at -15° C. under nitrogen, was added n-butyllithium (20 ml, 2.5M) dropwise and the solution stirred at -15° C. for 2 hours. The solution was then cooled to -78° C. and 6,6,6-trifluorohexylbromide (10.95 g) in dry tetrahydrofuran (20 ml) was added and solution stirred at -78° C. for 1 hour, allowed to warm to room temperature and stirred overnight. The reaction mixture was poured onto ice, extracted with ether (2×75 ml), dried over MgSO4 and evaporated under reduced pressure to give a brown oil. The oil was distilled under reduced pressure to give a colourless oil, b.p. 66° C./20 mm.

1. temperatureThe solution was then cooled to -78° C.
2. stirringsolution stirred at -78° C. for 1 hour
3. temperatureto warm to room temperature
4. stirringstirred overnight
5. additionThe reaction mixture was poured onto ice
6. extractionextracted with ether (2×75 ml)
7. dry with materialdried over MgSO4
8. customevaporated under reduced pressure
9. customto give a brown oil
10. distillationThe oil was distilled under reduced pressure
11. customto give a colourless oil, b.p. 66° C./20 mm

ORD record

ord-8d5b0fd280d744d0b8d4b7b7cd97a4e1

Source dataset

uspto-grants-1992_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05158971