Multi-step reaction with 10 steps
1: 1.) Mg, 2.) Br2 / 1.) THF, heating, 3 h, 2.)pentane, -78 deg C, 2 h
2: 27.4 g / NBS / CCl4 / 0.33 h / Heating; Irradiation
3: aq NaHCO3 / acetonitrile / 5 h / Heating
4: 1.) CH3I, 2.) aq NaOH / 1.) CH3NO2,acetone, MeOH, 2.) reflux, 24 h
5: 6.2 g / 50percent NaH, / tetrahydrofuran / 14 h / 25 °C
6: LiAlH4 / diethyl ether / 2 h / Heating
7: 64 percent / imidazole / dimethylformamide / 24 h / 25 °C
8: 1.) t-BuLI, ZnCl2, 2.) Pd.PPh3 / 1.) THF, -78 deg C, 2.) 25 deg C, 14 h
9: 87 percent / Bu4NF / tetrahydrofuran / 0.5 h
10: 82 percent / Ph3P, n-bromosuccinimide / tetrahydrofuran / 3 h / 25 °C
With
1H-imidazole; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; palladium-triphenylphosphine; tetrabutyl ammonium fluoride; bromine; tert.-butyl lithium; sodium hydride; sodium hydrogencarbonate; magnesium; triphenylphosphine; zinc(II) chloride; methyl iodide;
In
tetrahydrofuran; tetrachloromethane; diethyl ether; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4020(01)87577-3