1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione in tetrahydrofuran; dimethyl sulfoxide T=20°C; 2.8 h;

1: 91 percent / pyridine / 0 °C 2: 98 percent / LiAlH4 / diethyl ether / Heating View Scheme

bromine; bis(tri-n-butyltin)oxide in dichloromethane 3.5 h; Ambient temperature;

1: 70 percent / bis(tri-n-butyltin) oxide, bromine / CH2Cl2 / 3.5 h / Ambient temperature 2: 86 percent / diisopropylethylamine / CH2Cl2 / 20 h / Ambient temperature View Scheme