bromine; sodium acetate; acetic acid

potassium carbonate in N,N-dimethyl-formamide 1 h;

potassium carbonate in N,N-dimethyl-formamide 1 h;

1: 55 percent / K2CO3 / dimethylformamide / 1 h 2: 82 percent / Heating 3: 1.) BuLi / 1.) ether, hexane, -80 deg C, 15 min, 2.) ether, hexane, from -80 deg C to RT 4: aq. HCl / 2 h / 100 °C 5: 43 percent / ammonium acetate / 1 h / Heating 6: AlH3 / tetrahydrofuran / 0.5 h / Heating View Scheme

1: 36.0 g / K2CO3 / dimethylformamide / 1 h 2: 90 percent / Heating 3: 1.) BuLi / 1.) ether, hexane, -80 deg C, 15 min, 2.) ether, hexane, from -80 deg C to RT 4: aq. HCl / 2 h / 100 °C 5: 1.) BuLi / 1.) THF, hexane, from 0 deg C to RT, 2.) THF, hexane, reflux, 1 h 6: 1.) BH3*S(CH3)2, 2-methyl-2-butene, 2.) I2, NaOH / 1.) THF, RT, 2.) THF, MeOH 7: dimethylformamide / 1.5 h / Heating 8: 66percent aq. hydrazine / butan-1-ol / 2 h / 100 °C View Scheme

1: 36.0 g / K2CO3 / dimethylformamide / 1 h 2: 90 percent / Heating 3: 1.) BuLi / 1.) ether, hexane, -80 deg C, 15 min, 2.) ether, hexane, from -80 deg C to RT 4: aq. HCl / 2 h / 100 °C 5: 1.) BuLi / 1.) THF, hexane, from 0 deg C to RT, 2.) THF, hexane, reflux, 1 h 6: 1.) BH3*S(CH3)2, 2-methyl-2-butene, 2.) I2, NaOH / 1.) THF, RT, 2.) THF, MeOH 7: 66percent aq. hydrazine / butan-1-ol / 2 h / 100 °C View Scheme

in water