1: 27 percent / potassium permanganate / H2O / 1.) from RT to 43 deg C, 5 h, 2.) 45 deg C, overnight 2: thionyl chloride / Heating 3: ammonia gas / 1,2-dichloro-ethane / 0.5 h / -30 °C 4: 67 percent / bromine, aq. potassium hydroxide / 1.) RT, 1 h, 2.) 70 deg C, 15 min 5: 1.) 48-50percent fluoroboric acid, isoamyl nitrite / 1.) ethanol, -10 deg C, 20 min, 2.) a.) hexane, from 0 deg C to RT, b.) reflux, 30 min View Scheme

1: thionyl chloride / Heating 2: ammonia gas / 1,2-dichloro-ethane / 0.5 h / -30 °C 3: 67 percent / bromine, aq. potassium hydroxide / 1.) RT, 1 h, 2.) 70 deg C, 15 min 4: 1.) 48-50percent fluoroboric acid, isoamyl nitrite / 1.) ethanol, -10 deg C, 20 min, 2.) a.) hexane, from 0 deg C to RT, b.) reflux, 30 min View Scheme

1: ammonia gas / 1,2-dichloro-ethane / 0.5 h / -30 °C 2: 67 percent / bromine, aq. potassium hydroxide / 1.) RT, 1 h, 2.) 70 deg C, 15 min 3: 1.) 48-50percent fluoroboric acid, isoamyl nitrite / 1.) ethanol, -10 deg C, 20 min, 2.) a.) hexane, from 0 deg C to RT, b.) reflux, 30 min View Scheme

1: H2SO4; HNO3 2: calcium chloride; aqueous sodium nitrite solution; aqueous hydrochloric acid / Erhitzen des Reaktionsprodukts mit Wasser 3: phosphoryl chloride 4: palladium/charcoal; sodium acetate; acetic acid / Hydrogenation 5: ethyl nitrite / Erwaermen des erhaltenen Diazoniumsalzes mit Petrolaether View Scheme

1: calcium chloride; aqueous sodium nitrite solution; aqueous hydrochloric acid / Erhitzen des Reaktionsprodukts mit Wasser 2: phosphoryl chloride 3: palladium/charcoal; sodium acetate; acetic acid / Hydrogenation 4: ethyl nitrite / Erwaermen des erhaltenen Diazoniumsalzes mit Petrolaether View Scheme

tetrafluoroboric acid; isopentyl nitrite 1.) ethanol, -10 deg C, 20 min, 2.) a.) hexane, from 0 deg C to RT, b.) reflux, 30 min; Yield given. Multistep reaction;

1: 67 percent / bromine, aq. potassium hydroxide / 1.) RT, 1 h, 2.) 70 deg C, 15 min 2: 1.) 48-50percent fluoroboric acid, isoamyl nitrite / 1.) ethanol, -10 deg C, 20 min, 2.) a.) hexane, from 0 deg C to RT, b.) reflux, 30 min View Scheme

1: phosphoryl chloride 2: palladium/charcoal; sodium acetate; acetic acid / Hydrogenation 3: ethyl nitrite / Erwaermen des erhaltenen Diazoniumsalzes mit Petrolaether View Scheme

1: palladium/charcoal; sodium acetate; acetic acid / Hydrogenation 2: ethyl nitrite / Erwaermen des erhaltenen Diazoniumsalzes mit Petrolaether View Scheme

1: 66 percent / potassium permanganate / H2O / 3 h / Heating 2: 99 percent / diethyl ether / 1.) 0 deg C, 2.) RT, overnight View Scheme