titanium(III) chloride; water in ethanol pH=7; RefluxAlkaline aq. solutionInert atmosphere;

titanium tetrachloride; magnesium in diethyl ether; dichloromethane T=20°C; Inert atmosphere;

triethylamine in dichloromethane T=-5 - 0°C;

tetra-(n-butyl)ammonium iodide; caesium carbonate in N,N-dimethyl-formamide T=23°C; 46 h;

48 h; Ambient temperature;

1: 81 percent / methylcyclohexane / 24 h / Heating 2: 94 percent / acetone / 20 h 3: 1.) Na2CO3, 2.) conc. HCl, hydrazine hydrate / 1.) H2O, CH2Cl2; 2.) EtOH, overnight, reflux, 5 h, R. T. overnight 4: conc. HCl, NaNO2 / ethanol; H2O / 1 - 3 °C 5: K2CO3 6: 45percent HBr / acetic acid / 1.5 h View Scheme