1: 85 percent / EtONa, BHA, Pd(PPh3)4 / toluene; ethanol / 0.75 h / 65 °C 2: pyridinium tosylate, BHA, / ethanol / 3 h / 45 °C View Scheme

tetrakis(triphenylphosphine) palladium(0); 4-hydroxy-3-tert-butylanisole; sodium ethanolate in ethanol; toluene T=65°C; 0.75 h;

Multi-step reaction with 3 steps 1: 79 percent / diisobutylaluminum hydride / diethyl ether / 3.33 h / 25 - 40 °C2: pyridine, NBS / diethyl ether / 1.25 h / 25 - 30 °C / Irradiation3: 1.) Br2, 2.) tetrabutylammonium fluoride trihydrate / 1.) CH2Cl2, -78 deg C, 2.) THF, CH2Cl2, -20 deg C  

Multi-step reaction with 2 steps 1: pyridine, NBS / diethyl ether / 1.25 h / 25 - 30 °C / Irradiation2: 1.) Br2, 2.) tetrabutylammonium fluoride trihydrate / 1.) CH2Cl2, -78 deg C, 2.) THF, CH2Cl2, -20 deg C  

With  tetrabutyl ammonium fluoride; bromine  1.) CH2Cl2, -78 deg C, 2.) THF, CH2Cl2, -20 deg C;  Yield given. Multistep reaction;