manganese(IV) oxide in dichloromethane T=20°C; 12 h;

N-bromosuccinmide in acetonitrile T=0 - 20°C;

1.1: Mg / tetrahydrofuran; diethyl ether / 1.5 h / Heating 1.2: 82 percent / tetrahydrofuran; diethyl ether / 2 h / 20 °C 2.1: 84 percent / Br2 / dioxane / 168 h / 20 °C 3.1: 72 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C 4.1: 87 percent / MnO2 / CH2Cl2 / 12 h / 20 °C View Scheme

1: 84 percent / Br2 / dioxane / 168 h / 20 °C 2: 72 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C 3: 87 percent / MnO2 / CH2Cl2 / 12 h / 20 °C View Scheme

1: 72 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C 2: 87 percent / MnO2 / CH2Cl2 / 12 h / 20 °C View Scheme

1.1: POCl3 / 0.25 h / cooling 1.2: 85 percent / dimethylformamide / 100 - 110 °C 2.1: 80 percent / N-bromosuccinimide / acetonitrile / 0 - 20 °C View Scheme

1: aq. m-CPBA / CH2Cl2 / 12 h / 20 °C 2: 1.68 g / K2CO3 / methanol / 0.25 h / 20 °C View Scheme

toluene-4-sulfonic acid in benzene 9 h; Heating;

1: 90 percent / PTSA monohydrate / benzene / 9 h / Heating View Scheme