benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine in N,N-dimethyl-formamide T=20°C; 16 h;

1: 4-Bromo-2-fluorobenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane T=20°C; 0.5 h; 2: methylamine With triethylamine in tetrahydrofuran; dichloromethane T=20°C; 0.166667 h; 3: With hydrogenchloride in tetrahydrofuran; dichloromethane; water T=20°C;

in isopropanol acetate; water T=2 - 35°C; 1.08333 h; Inert atmosphereIndustry scale;

1: thionyl chloride / N,N-dimethyl-formamide; isopropanol acetate / 4.58 h / 21 - 72 °C / Inert atmosphere; Industry scale 2: water; isopropanol acetate / 1.08 h / 2 - 35 °C / Inert atmosphere; Industry scale View Scheme

1.1: potassium carbonate / copper(l) chloride / N,N-dimethyl-formamide; water / 30 °C 1.2: 105 °C / Inert atmosphere 1.3: pH 4 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 30 °C 2.2: 1.08 h / 32 - 40 °C 3.1: dimethyl sulfoxide; isopropanol acetate / 17.5 h / 83 - 84 °C View Scheme

1.1: potassium carbonate / copper(l) chloride / N,N-dimethyl-formamide; water / 30 °C 1.2: 105 °C / Inert atmosphere 1.3: pH 4 2.1: potassium carbonate / N,N-dimethyl-formamide; water / 30 °C 2.2: 1.08 h / 32 - 40 °C View Scheme

1: With potassium carbonate; copper(l) chloride in water; N,N-dimethyl-formamide T=30°C; 2: With 2-acetyl-1-cyclohexanone in water; N,N-dimethyl-formamide T=105°C; Inert atmosphere; 3: With citric acid in isopropanol acetate; water pH=4;