1: 2-ethoxy-3-fluorophenol With potassium carbonate in acetone 0.5 h; Inert atmosphereReflux; 2: diethyl sulphate in acetone T=56°C; 5 h; Inert atmosphere;

sodium hydroxide in ethanol T=10°C; 5 h; Heating / reflux; Product distribution / selectivity;

sodium hydroxide in ethanol T=10°C; 3 h; Heating / reflux; Product distribution / selectivity;

tetrabutylammomium bromide; potassium carbonate in tert-butyl methyl ether 3.75 h; Reflux;

potassium carbonate in DMF (N,N-dimethyl-formamide) T=0 - 20°C;

1.1: potassium carbonate / 1-methyl-pyrrolidin-2-one / 30 - 70 °C / Inert atmosphere 1.2: 60 - 80 °C / Inert atmosphere 2.1: 1-methyl-pyrrolidin-2-one / 180 - 210 °C / Inert atmosphere 2.2: 60 - 80 °C / Inert atmosphere 2.3: 100 - 110 °C / Inert atmosphere 3.1: N-benzyl-N,N,N-triethylammonium chloride; potassium permanganate / dansyl cadaverine / 2 h / 0 °C 4.1: formic acid; dihydrogen peroxide / dansyl cadaverine / 24 h / 20 - 40 °C 4.2: 1 h / 10 - 20 °C / Industry scale 4.3: pH 2 - 4 5.1: potassium carbonate / N,N-dimethyl-formamide / 65 - 70 °C View Scheme

1.1: AlCl3, aluminium chloride / chlorobenzene / 120 °C / |Inert atmosphere; |Large scale 2.1: sodium hydroxide / water / 1 h / 40 - 45 °C / |Inert atmosphere 2.2: 3 h / 25 °C / |Inert atmosphere 3.1: potassium carbonate; tetrabutylammomium bromide / tert-butyl methyl ether / 3.75 h / |Reflux View Scheme

1.1: sodium hydroxide / water / 1 h / 40 - 45 °C / |Inert atmosphere 1.2: 3 h / 25 °C / |Inert atmosphere 2.1: potassium carbonate; tetrabutylammomium bromide / tert-butyl methyl ether / 3.75 h / |Reflux View Scheme

1.1: 1-methyl-pyrrolidin-2-one / 180 - 210 °C / Inert atmosphere 1.2: 60 - 80 °C / Inert atmosphere 1.3: 100 - 110 °C / Inert atmosphere 2.1: N-benzyl-N,N,N-triethylammonium chloride; potassium permanganate / dansyl cadaverine / 2 h / 0 °C 3.1: formic acid; dihydrogen peroxide / dansyl cadaverine / 24 h / 20 - 40 °C 3.2: 1 h / 10 - 20 °C / Industry scale 3.3: pH 2 - 4 4.1: potassium carbonate / N,N-dimethyl-formamide / 65 - 70 °C View Scheme

1.1: N-benzyl-N,N,N-triethylammonium chloride; potassium permanganate / dansyl cadaverine / 2 h / 0 °C 2.1: formic acid; dihydrogen peroxide / dansyl cadaverine / 24 h / 20 - 40 °C 2.2: 1 h / 10 - 20 °C / Industry scale 2.3: pH 2 - 4 3.1: potassium carbonate / N,N-dimethyl-formamide / 65 - 70 °C View Scheme