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

참여 물질

반응 조건

반응 단계

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.

출처 및 근거