1: 1-N-allyl-2,6-dibromo-4-fluoroaniline With triethylamine; tris-(o-tolyl)phosphine; palladium diacetate in acetonitrile 3 h; Heating / reflux; 2: acrylic acid in acetonitrile T=20°C; Heck Reaction; 3.5 h; Heating / reflux; 3: With hydrogenchloride in water pH=2 - 3;

1: With methanol; sodium hydroxide; water in tetrahydrofuran T=20°C; 15 h; 2: With hydrogenchloride; water in tetrahydrofuran; methanol pH=2 - 3; Product distribution / selectivity;

triethylamine; palladium diacetate; tris-(o-tolyl)phosphine in acetonitrile T=20°C; Heck Reaction; 3.5 h; Heating / reflux; Product distribution / selectivity;

1.1: potassium tert-butylate / tetrahydrofuran / 0.25 h / 20 °C / |Inert atmosphere; |Large scale 1.2: 1.58 h / 10 - 20 °C / |Inert atmosphere; |Large scale 2.1: palladium diacetate; tris-(o-tolyl)phosphine; triethylamine / acetonitrile / 4 h / 75 °C / |Inert atmosphere; |Large scale 2.2: 38 h / |Inert atmosphere; |Reflux; |Large scale View Scheme

1.1: palladium diacetate; tris-(o-tolyl)phosphine; triethylamine / acetonitrile / 3.25 h / |Inert atmosphere; |Reflux 1.2: 18.5 h / |Inert atmosphere 2.1: sodium hydroxide; water / tetrahydrofuran; methanol / 20 °C / |Inert atmosphere View Scheme

1: tetrahydrofuran / 1 h / -50 °C 2: palladium diacetate; tris-(o-tolyl)phosphine; triethylamine / acetonitrile / |Inert atmosphere; |Reflux; |Large scale 3: sodium hydroxide; water / tetrahydrofuran; methanol / 20 °C / |Inert atmosphere View Scheme

1: palladium diacetate; tris-(o-tolyl)phosphine; triethylamine / acetonitrile / |Inert atmosphere; |Reflux; |Large scale 2: sodium hydroxide; water / tetrahydrofuran; methanol / 20 °C / |Inert atmosphere View Scheme