p-benozquinone; lithium chloride; palladium dichloride in tetrahydrofuran 16 h; Heating;

1: 2-bromo-5-chloro-4-fluoroaniline With palladium diacetate; triphenylphosphine in tetrahydrofuran T=20°C; 0.0833333 h; 2: vinyl-magnesium bromide in tetrahydrofuran Grignard reaction; 1 h; Heating;

1.1: 41 percent / bromine; pyridine / CH2Cl2 / 1 h / 0 °C 2.1: triphenylphosphine; palladium(II) acetate / tetrahydrofuran / 0.08 h / 20 °C 2.2: 62 percent / tetrahydrofuran / 1 h / Heating View Scheme