chlorine in tetrachloromethane

sodium hydroxide in ethanol T=20°C; 2 h;

N-iodo-succinimide; toluene-4-sulfonic acid in acetonitrile T=20°C; 14 h; regioselective reaction;

iodine; thallous acetate in dichloromethane 48 h; Ambient temperature;

iodine in dichloromethane 24 h; Ambient temperature;

N-iodo-succinimide in acetonitrile T=20°C; 14 h;

1.1: 98 percent / DMAP / tetrahydrofuran / 24 h / 60 °C 2.1: N,N,N',N'-tetramethylethylenediamine; TMSOTf / diethyl ether; pentane / 0.58 h / 0 - 20 °C 2.2: N,N,N',N'-tetramethylethylenediamine; n-BuLi / diethyl ether; pentane / 1 h / -78 °C 2.3: 86 percent / I2 / diethyl ether; pentane / 1 h / -78 °C 3.1: 94 percent / 2 M NaOH / ethanol / 2 h / 20 °C View Scheme

1.1: N,N,N',N'-tetramethylethylenediamine; TMSOTf / diethyl ether; pentane / 0.58 h / 0 - 20 °C 1.2: N,N,N',N'-tetramethylethylenediamine; n-BuLi / diethyl ether; pentane / 1 h / -78 °C 1.3: 86 percent / I2 / diethyl ether; pentane / 1 h / -78 °C 2.1: 94 percent / 2 M NaOH / ethanol / 2 h / 20 °C View Scheme