反应详情

温度

-15 °C

To a suspension of N-chlorosuccinimide (7.8 g) in benzene (30 ml) was added dropwise, a solution of thiophenol (5.51 g) in benzene (20 ml) at room temperature. After 1 hour, the suspension was filtered, the filter pad washed with benzene and the filtrate evaporated under reduced pressure to give an orange oil. The oil was dissolved in dry tetrahydrofuran (20 ml) and added dropwise to a solution of 2-thienyl-lithium (prepared by the addition of n-butyllithium (20 ml, 2.5M) to thiophene (4.2 g) in dry tetrahydrofuran (30 ml) at -15° C. under nitrogen and stirred for 2 hours) at -15° C. under N2. The solution was stirred for 1 hour, allowed to warm to room temperature and stirred overnight. The reaction mixture was poured on to 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 C60-40/60H column using petroleum ether (40°-60° C.) to give a colourless oil, b.p. 161° C./20 mm pressure.

1. additionwas added dropwise
2. customat room temperature
3. filtrationthe suspension was filtered
4. washthe filter pad washed with benzene
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 on to 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
16. custompetroleum ether (40°-60° C.)
17. customto give a colourless oil, b.p. 161° C./20 mm pressure