1: 1.) Br2, 2.) tetrabutylammonium fluoride trihydrate / 1.) CH2Cl2, -78 deg C, 2.) THF, CH2Cl2, -20 deg C 2: 63 percent / EtONa, BHA, Pd(PPh3)4 / toluene; ethanol / 0.75 h / 65 °C 3: 85 percent / pyridinium tosylate, BHA, / ethanol / 3 h / 45 °C 4: pyridine / -10 °C View Scheme

1: 1.) Br2, 2.) tetrabutylammonium fluoride trihydrate / 1.) CH2Cl2, -78 deg C, 2.) THF, CH2Cl2, -20 deg C 2: 87 percent / EtONa, BHA, Pd(PPh3)4 / toluene; ethanol / 0.75 h / 65 °C 3: pyridinium tosylate, BHA, / ethanol / 3 h / 45 °C View Scheme

1: pyridine, NBS / diethyl ether / 1.25 h / 25 - 30 °C / Irradiation 2: 1.) Br2, 2.) tetrabutylammonium fluoride trihydrate / 1.) CH2Cl2, -78 deg C, 2.) THF, CH2Cl2, -20 deg C 3: 85 percent / EtONa, BHA, Pd(PPh3)4 / toluene; ethanol / 0.75 h / 65 °C 4: pyridinium tosylate, BHA, / ethanol / 3 h / 45 °C View Scheme

1: 1.) Br2, 2.) tetrabutylammonium fluoride trihydrate / 1.) CH2Cl2, -78 deg C, 2.) THF, CH2Cl2, -20 deg C 2: 10 percent / EtONa, BHA, Pd(PPh3)4 / toluene; ethanol / 0.75 h / 65 °C View Scheme

1: 1.) Br2, 2.) tetrabutylammonium fluoride trihydrate / 1.) CH2Cl2, -78 deg C, 2.) THF, CH2Cl2, -20 deg C 2: 63 percent / EtONa, BHA, Pd(PPh3)4 / toluene; ethanol / 0.75 h / 65 °C 3: 85 percent / pyridinium tosylate, BHA, / ethanol / 3 h / 45 °C View Scheme

With  diisobutylaluminium hydride in  diethyl ether T=25 - 40°C; 3.33333 h;   

With  2,2'-azo-bisisobutyronitrile; thiophenol in  benzene  

Multi-step reaction with 2 steps 1: Br2 / CH2Cl2 2: n-Bu4NF / tetrahydrofuran  

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