1: p-TsOH, hexamethyldisilazane, NH3 / 120 h / 155 - 160 °C 2: 50percent aq. MeOH / 4 h / Heating 3: HBr / dioxane / 20 h 4: N,N-dimethyl-acetamide / 72 h / Ambient temperature View Scheme

1: 83 percent / BCl3 / CH2Cl2 / a) -78 deg C, 3 h, b) RT, overnight 2: 80 percent / pyridine / 48 h / Ambient temperature 3: p-TsOH, hexamethyldisilazane, NH3 / 120 h / 155 - 160 °C 4: 50percent aq. MeOH / 4 h / Heating 5: HBr / dioxane / 20 h 6: N,N-dimethyl-acetamide / 72 h / Ambient temperature View Scheme

1: 89 percent / NaNO2, AcOH, Ac2O / 2 h / Ambient temperature 2: 90 percent / Heating 3: 83 percent / BCl3 / CH2Cl2 / a) -78 deg C, 3 h, b) RT, overnight 4: 80 percent / pyridine / 48 h / Ambient temperature 5: p-TsOH, hexamethyldisilazane, NH3 / 120 h / 155 - 160 °C 6: 50percent aq. MeOH / 4 h / Heating 7: HBr / dioxane / 20 h 8: N,N-dimethyl-acetamide / 72 h / Ambient temperature View Scheme

1: 90 percent / Heating 2: 83 percent / BCl3 / CH2Cl2 / a) -78 deg C, 3 h, b) RT, overnight 3: 80 percent / pyridine / 48 h / Ambient temperature 4: p-TsOH, hexamethyldisilazane, NH3 / 120 h / 155 - 160 °C 5: 50percent aq. MeOH / 4 h / Heating 6: HBr / dioxane / 20 h 7: N,N-dimethyl-acetamide / 72 h / Ambient temperature View Scheme

in N,N-dimethyl acetamide 72 h; Ambient temperature; Yield given;

1: 87 percent / 1 N NaOH / dimethylsulfoxide / 6 h 2: 94 percent / NaBH3CN / H2O / 23 h / pH 6.4 View Scheme

1: 87 percent / 1 N NaOH / dimethylsulfoxide / 6 h 2: 94 percent / NaBH3CN / H2O / 23 h / pH 6.4 3: 64 percent / 1 N NaOH / 4.25 h / Heating View Scheme