Diazotization;

1: 3-hydroxy-6-nitro-toluene With bromine; acetic acid 2: methyl iodide With potassium carbonate in acetone T=20°C; Reflux; 3: With triphenyl phosphite; ammonium metavanadate; hydrogen; platinum on carbon in dichloromethane P=4395.87 Torr;

1: dichloromethane / 3 h / 25 °C / |Large scale 2: acetic acid; bromine / 10 h / 8 - 30 °C / |Large scale 3: hydrogenchloride / methanol; water / |Reflux; |Large scale View Scheme

1: acetic acid; bromine / 10 h / 8 - 30 °C / |Large scale 2: hydrogenchloride / methanol; water / |Reflux; |Large scale View Scheme

hydrogenchloride; methanol; iron

1: chloroform; bromine / 40 - 50 °C 2: K2CO3; benzene 3: iron; methanol; aqueous hydrochloric acid View Scheme

1: K2CO3; benzene 2: iron; methanol; aqueous hydrochloric acid View Scheme

1.1: hydrogenchloride; sodium nitrite / water / 0.5 h / 0 °C / |Large scale 1.2: 1 h / 0 - 5 °C / |Large scale 1.3: 25 °C / |Inert atmosphere; |Large scale 2.1: potassium tert-butylate / tetrahydrofuran / 2.5 h / 20 - 25 °C / |Large scale 3.1: AlCl3, aluminium chloride / toluene / 5 h / 110 °C / |Large scale 3.2: |Large scale 4.1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 15 h / 60 - 65 °C / |Large scale View Scheme