sodium hydride; dimethyl sulfoxide in tetrahydrofuran T=20°C; 2 h;

sodium hydride in tetrahydrofuran; N,N-dimethyl-formamide

1: 86 percent / triphenyl phosphine; Et3N / CCl4 / 3 h / Heating 2: 92 percent / N-bromosuccinimide; benzoyl peroxide / CCl4 / Heating 3: 82 percent / magnesium / tetrahydrofuran / 2 h / 0 °C 4: 93 percent / NaH; Me2SO / various solvent(s); tetrahydrofuran / 2 h / 20 °C View Scheme

N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile in tetrachloromethane Heating;