sulfuric acid T=20°C;

sodium hydride in N,N-dimethyl-formamide T=20 - 30°C;

1: propionic acid methyl ester With sodium hexamethyldisilazane in toluene T=-60°C; 1.5 h; Inert atmosphereSealed tube; 2: With zinc(II) chloride in tetrahydrofuran; toluene T=-35°C; 1 h; Inert atmosphereSealed tube; 3: 1-bromo-4-nitro-benzene With (1,2,3,4,5-pentaphenylferrocen-1'-yl)-di-tert-butylphosphine; bis(dibenzylideneacetone)-palladium(0) in tetrahydrofuran; toluene T=-15 - 20°C; 4 h; Inert atmosphereSealed tube;

tris(dimethylamino)-sulphonium difluorotrimethylsilicate; bromine 1)THF, acetonitrile, -40 deg C, 30-60 min 2)-78 deg C; Multistep reaction. Title compound not separated from byproducts;

1: NaOH / dimethylformamide; methanol; H2O / 1 h / 50 °C 2: concd. H2SO4 / 3 h / Heating View Scheme

1: 1.) NaH / 1.) DMF, 50 deg C, 20 min, 2.) DMF, 100 deg C, 2 h 2: NaOH / dimethylformamide; methanol; H2O / 1 h / 50 °C 3: concd. H2SO4 / 3 h / Heating View Scheme

tris(dimethylamino)-sulphonium difluorotrimethylsilicate; bromine 1.) THF, acetonitrile, -40 to -10 deg C, 1-2 h; 2.) THF, acetonitrile, cyclohexane, -78 deg C; Yield given. Multistep reaction;

caesium carbonate in N,N-dimethyl-formamide T=60°C; Inert atmosphere;

potassium hydroxide in tetrahydrofuran; methanol 6 h;

hydrogenchloride; sodium hydroxide; NaH in nitrobenzene; N,N-dimethyl-formamide; mineral oil