1: 2,3-dibromotoluene With isopropylmagnesium chloride in tetrahydrofuran T=-40°C; 2: carbon dioxide in tetrahydrofuran Further stages.;

potassium permanganate in water; acetone 1 h; Heating; Yield given;

1: NBS, benzoyl peroxide / CCl4 / 3 h / Heating 2: 1.) hexamine; 2.) conc. HCl / 1.) CHCl3, reflux, 1 h; 2.) 50percent aq. AcOH, reflux, 1 h 3: KMnO4 / acetone; H2O / 1 h / Heating View Scheme

1: 1.) hexamine; 2.) conc. HCl / 1.) CHCl3, reflux, 1 h; 2.) 50percent aq. AcOH, reflux, 1 h 2: KMnO4 / acetone; H2O / 1 h / Heating View Scheme

2-ethoxy-ethanol Erhitzen des Reaktionsgemisches mit wss. HCl;

1: thionyl chloride / 3 h / Reflux 2: N-bromosuccinmide; dibenzoyl peroxide / tetrachloromethane / 5 h / 80 - 85 °C 3: water; calcium carbonate / tetrahydrofuran / 5 h / 100 °C View Scheme

1.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 0.25 h / Cooling with ice 1.2: Cooling with ice 2.1: manganese(IV) oxide / chloroform View Scheme

1: triethylamine / dichloromethane / 0.17 h / 0 °C 2: ammonium hydroxide / 0.03 h / 0 °C 3: 2,4,6-trichloro-1,3,5-triazine / N,N-dimethyl-formamide / 0 - 20 °C View Scheme

hydrogen azide; sulfuric acid

1: triethylamine / dichloromethane / 0.17 h / 0 °C 2: ammonium hydroxide / 0.03 h / 0 °C 3: 2,4,6-trichloro-1,3,5-triazine / N,N-dimethyl-formamide / 0 - 20 °C 4: N-bromosuccinmide; dibenzoyl peroxide / tetrachloromethane / 16 h / Reflux; Inert atmosphere 5: N,N-dimethyl-formamide / 1 h / 80 °C 6: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 16 h / Reflux; Inert atmosphere View Scheme