1: 79.5 percent / Et3N / diethyl ether / 0.5 h / Ambient temperature 2: 77.3 percent / NaBH4, NaH, 2-propanol / dioxane / 1.) 70 deg C, 2.) reflux, 1 h 3: 94.8 percent / m-chloroperbenzoic acid / CH2Cl2 / Ambient temperature 4: tert-BuOK / dimethylsulfoxide; tetrahydrofuran / 0.17 h / Ambient temperature 5: Al-Hg / tetrahydrofuran; H2O / 0.67 h / Heating View Scheme

thionyl chloride

1: hydrogen bromide 2: thionyl chloride View Scheme

1: aq. HNO3 2: SOCl2 View Scheme

triethylamine in chloroform T=0 - 20°C; 17 h;

tin(IV) chloride in benzene -3 deg C-0 deg C -> 20 deg C;