K3PO4*7H2O; oxygen; palladium diacetate in isopropyl alcohol T=80°C; Suzuki Coupling;

[1,4-bis-(diphenylphosphine)butane]palladium (II) dichloride in tetrahydrofuran 6 h; Heating / reflux;

n-butyllithium; fluoropicoline 1.) diethyl ether, -65 deg C, 1 h, 2.) diethyl ether, -40 deg C to -30 deg C, 30 min; Yield given. Multistep reaction;

potassium permanganate in water 1.75 h; Heating;

1: 60 percent / potassium permanganate / H2O / 1.75 h / Heating 2: 85 percent / polyphosphoric acid / 4.5 h / 210 °C 3: 80 percent / hydrazine monohydrate / bis-(2-hydroxy-ethyl) ether / 4 h / 180 °C View Scheme