potassium tert-butylate in tert-butyl alcohol T=20°C;

potassium tert-butylate; carbamic acid ethyl ester; sodium nitrite Multistep reaction;

1: 95 percent / SOCl2 / 8 h / 20 °C 2: 30 percent / AgBF4 / dioxane / 24 h / 100 °C 3: 90 percent / NaNO2 / acetic acid; acetic anhydride / 24 h / 20 °C 4: 15 percent / t-BuOK / 2-methyl-propan-2-ol / 20 °C View Scheme

1: 90 percent / NaNO2 / acetic acid; acetic anhydride / 24 h / 20 °C 2: 15 percent / t-BuOK / 2-methyl-propan-2-ol / 20 °C View Scheme

1: 79 percent / aq. H3PO2; NaNO2 / H2O / 20 °C 2: 95 percent / SOCl2 / 8 h / 20 °C 3: 30 percent / AgBF4 / dioxane / 24 h / 100 °C 4: 90 percent / NaNO2 / acetic acid; acetic anhydride / 24 h / 20 °C 5: 15 percent / t-BuOK / 2-methyl-propan-2-ol / 20 °C View Scheme

1: 72 percent / NaBH4 / ethanol / Heating 2: 98 percent / aq. HCl; Br2 / tetrahydrofuran; H2O 3: 79 percent / aq. H3PO2; NaNO2 / H2O / 20 °C 4: 95 percent / SOCl2 / 8 h / 20 °C 5: 30 percent / AgBF4 / dioxane / 24 h / 100 °C 6: 90 percent / NaNO2 / acetic acid; acetic anhydride / 24 h / 20 °C 7: 15 percent / t-BuOK / 2-methyl-propan-2-ol / 20 °C View Scheme

1: 98 percent / aq. HCl; Br2 / tetrahydrofuran; H2O 2: 79 percent / aq. H3PO2; NaNO2 / H2O / 20 °C 3: 95 percent / SOCl2 / 8 h / 20 °C 4: 30 percent / AgBF4 / dioxane / 24 h / 100 °C 5: 90 percent / NaNO2 / acetic acid; acetic anhydride / 24 h / 20 °C 6: 15 percent / t-BuOK / 2-methyl-propan-2-ol / 20 °C View Scheme