1: With hydrogenchloride; sodium nitrite in water T=0°C; Diazotization; 1 h; 2: With potassium iodide in water T=25°C; Iodination; Sandmeyer reaction; 12 h; Further stages.;

1: 100 percent / H2 / Pd/C 2: NaNO2; H2SO4 3: KI View Scheme

iodine; periodic acid in sulfuric acid; water; acetic acid 6 h;

boron tribromide in dichloromethane

1: 2-iodo-5-methoxytoluene With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 1 h; Inert atmosphere; 2: N,N-dimethyl-formamide in tetrahydrofuran; hexane T=-78 - 20°C; Inert atmosphere; 3: With water; ammonium chloride in tetrahydrofuran; hexane T=0°C; Saturated solution;