N-bromosuccinmide in chloroform

bromine; triphenylphosphine in dichloromethane T=10°C; 0.333333 h; Inert atmosphere;

1.1: n-BuLi; DMSO / hexane / 1 h / 20 °C 1.2: 89 percent / dimethylsulfoxide; hexane 2.1: N-bromosuccinimide / CHCl3 View Scheme

1.1: potassium carbonate / acetonitrile / Inert atmosphere; Reflux 2.1: Grubb's 2nd generation catalyst / dichloromethane / 20 °C / Inert atmosphere 3.1: [Ir(C8H12)((Ph)2PCH2C7H7NSPh)]BArF; hydrogen / dichloromethane / 20 h / 20 °C / 37503.8 Torr / Autoclave 4.1: Na naphthalenide / tetrahydrofuran / -78 °C / Inert atmosphere 4.2: -78 °C View Scheme