Benzothiophene, 4,5,6,7-tetrahydro- → 2-Bromo-4,5,6,7-tetrahydrobenzo(b)thiophene
Reaktionsgleichung
[S:1]1[CH:5]=[CH:4][C:3]2[CH2:6][CH2:7][CH2:8][CH2:9][C:2]1=2.[Br:10]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:10][C:5]1[S:1][C:2]2[CH2:9][CH2:8][CH2:7][CH2:6][C:3]=2[CH:4]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
4,5,6,7-Tetrahydrobenzo[b]thiophene (0.252 g, 1.79 mmol) was dissolved in chloroform (10 mL), cooled to 0° C. and N-bromosuccinimide (0.334 g, 1.88 mmol) was added. The reaction mixture was stirred at 0° C. for 1 h then at ambient temperature for 1.75 h and then heated at 40° C. for a further 4 h. The reaction mixture was cooled to room temperature, concentrated in vacuo and the residue diluted with water and extracted with diethyl ether (4×10 mL). The combined organic phase was washed with water and brine, dried over sodium sulfate, filtered and evaporated to afford the title compound (0.35 g, 88%) as a brown oil. 1H NMR (CDCl3, 300 MHz): 6.69 (s, 1H), 2.73-2.59 (m, 2H), 2.58-2.49 (m, 2H), 1.88-1.70 (m, 4H).