1: 2.) Pd/C / 1.) nitration, 2.) toluene-EtOH 2: 51 percent / H2 / Pd/C / ethanol; toluene 3: 40 percent / NaNO2, conc. H2SO4, phosphoric acid, KI / 0 °C 4: 1.3 g / NBS, dibenzoyl peroxide / CCl4 / 24 h / Heating View Scheme

1: 51 percent / H2 / Pd/C / ethanol; toluene 2: 40 percent / NaNO2, conc. H2SO4, phosphoric acid, KI / 0 °C 3: 1.3 g / NBS, dibenzoyl peroxide / CCl4 / 24 h / Heating View Scheme

N-bromosuccinmide; dibenzoyl peroxide in tetrachloromethane 24 h; Heating;

1: 40 percent / NaNO2, conc. H2SO4, phosphoric acid, KI / 0 °C 2: 1.3 g / NBS, dibenzoyl peroxide / CCl4 / 24 h / Heating View Scheme