p-Chlorothiophenol → 2-[(4-Chlorophenyl)thio]thiophene

Temperatur

-15 °C

To a suspension of N-chlorosuccinimide (10.78 g) in dry toluene (45 ml) was added dropwise, a solution of 4-chlorothiophenol (9.84 g) in dry toluene (35 ml) at room temperature. After 1 hour, the suspension was filtered, the filter pad washed with toluene (100 ml) and the filtrate evaporated under reduced pressure to give an orange oil. The oil was dissolved in dry tetrahydrofuran (40 ml) and added dropwise to a solution of 2-thienyllithium (prepared by the addition of n-butyllithium (27.2 ml, 2.5M) to thiophene (5.72 g) in dry tetrahydrofuran (60 ml) at -15° C. under nitrogen and stirred for 2 hours) at -15° C. under nitrogen. The solution was stirred for 1 hour, allowed to warm to room temperature and stirred overnight. The reaction mixture was poured onto ice, extracted with ether (3×100 ml), dried over MgSO4 and evaporated under reduced pressure to give a brown oil. The oil was flash chromatographed on a Sorbsil C 60-40/60H column using petroleum ether (40°-60° C.) to give a colourless oil.

1. additionwas added dropwise
2. customat room temperature
3. filtrationthe suspension was filtered
4. washthe filter pad washed with toluene (100 ml)
5. customthe filtrate evaporated under reduced pressure
6. customto give an orange oil
7. stirringThe solution was stirred for 1 hour
8. temperatureto warm to room temperature
9. stirringstirred overnight
10. additionThe reaction mixture was poured onto ice
11. extractionextracted with ether (3×100 ml)
12. dry with materialdried over MgSO4
13. customevaporated under reduced pressure
14. customto give a brown oil
15. customchromatographed on a Sorbsil C 60-40/60H column
16. custompetroleum ether (40°-60° C.)
17. customto give a colourless oil

ORD-Eintrag

ord-80791023850f4b78a547aef6ed271ca6

Quelldatensatz

uspto-grants-1992_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05158971