o-Toluenesulfonyl chloride → 4-Bromo-1-(2-methyl-benzenesulfonyl)-1H-indole
Reaktionsgleichung
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[CH3:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[S:18](Cl)(=[O:20])=[O:19]>>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[S:18]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH3:11])(=[O:20])=[O:19]Komponenten
3
Versuchsvorschrift
The compound was prepared from 4-bromoindole (1.02 g, 5.25 mmol) and o-methylbenzenesulfonyl chloride (a 9:1 mixture of ortho and para methyl isomers) (1.29 g, 6.78 mmol) according to method 4. Purification by column chromatography (SiO2, CH2Cl2:heptane) gave 1.6 g (87%) of the title compound which contains ca 10% of the p-methyl isomer) as a light purple viscous oil: 1H NMR (CD3OD) δ 7.94–6.68 (m, 9H), 2.52 (s, 3H); MS (ESI) 352.3 (M+H)+; Purity (HPLC) >95%.
Aufarbeitung
- additiona 9:1 mixture of ortho and para methyl isomers) (1.29 g, 6.78 mmol)
- customPurification by column chromatography (SiO2, CH2Cl2:heptane)