Benzyl Bromide → O-Benzyl methanesulfonothioate
Reaktionsgleichung
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][S:10](=[S:13])([O-:12])=[O:11].[Na+]>CCO>[CH3:9][S:10](=[S:13])([O:12][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:11]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Benzyl bromide (9.07 g, 0.053 mol) was slowly added to a suspension of sodium methanethiosulfonate (7.10 g, 0.0530 mol) in absolute EtOH (100 mL) and the reaction mixture was heated at reflux overnight. The reaction mixture was cooled with an ice bath and the solid (sodium bromide and sodium methanethiosulfonate) was filtered off. The filtrate was concentrated to give a crude product which was mainly the desired product. Pure product was obtained by flash chromatography on silica gel with EtOAc-hexanes (1:6) (7.92 g, 74%). The product was further purified by recrystallization from absolute ethanol. mp 39.5-40.2° C. (lit. 40-42.5° C.) IR (KBr): 3089, 3068, 3017, 3000, 2981, 2936, 2918, 1602, 1582, 1496, 1305, 1131, 960, 771, 741, 702 cm−1. 1H NMR (200 MHz, CDCl3): δ 7.38 (m, 5H, phenyl), 4.38 (s, 2H, SCH2), 2.91 (s, 3H, CH3SO2). 13C NMR (50 MHz, CDCl3): δ 135.12, 129.14, 129.03, 128.26, 51.09, 40.79.