potassium hydroxide in water; dimethyl sulfoxide T=20°C; 2 h;

2,2,6,6-tetramethylpiperidinyl-lithium in tetrahydrofuran T=20°C; Title compound not separated from byproducts;

1: i-Pr2NEt / CH2Cl2 / 24 h / 20 °C 2: 1.10 g / CBr4; PPh3 / CH2Cl2 / 0.5 h / 0 °C 3: 94 percent / potassium hexamethyldisilazide / dimethylformamide; tetrahydrofuran / 0.5 h / -60 °C View Scheme

1: K2CO3; NaI / dimethylformamide / 2 h / 70 °C 2: i-Pr2NEt / CH2Cl2 / 24 h / 20 °C 3: 1.10 g / CBr4; PPh3 / CH2Cl2 / 0.5 h / 0 °C 4: 94 percent / potassium hexamethyldisilazide / dimethylformamide; tetrahydrofuran / 0.5 h / -60 °C View Scheme

1: i-Pr2NEt / CH2Cl2 / 24 h / 20 °C 2: 1.10 g / CBr4; PPh3 / CH2Cl2 / 0.5 h / 0 °C 3: 94 percent / potassium hexamethyldisilazide / dimethylformamide; tetrahydrofuran / 0.5 h / -60 °C View Scheme

1: N-ethyl-N,N-diisopropylamine / dichloromethane / Inert atmosphere 2: 10 palladium on activated charcoal; hydrogen / Inert atmosphere 3: carbon tetrabromide; triphenylphosphine / dichloromethane / Inert atmosphere 4: potassium hexamethylsilazane / N,N-dimethyl-formamide / 0.5 h / -60 °C / Inert atmosphere View Scheme

1: potassium carbonate / N,N-dimethyl-formamide / 70 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine / dichloromethane / Inert atmosphere 3: 10 palladium on activated charcoal; hydrogen / Inert atmosphere 4: carbon tetrabromide; triphenylphosphine / dichloromethane / Inert atmosphere 5: potassium hexamethylsilazane / N,N-dimethyl-formamide / 0.5 h / -60 °C / Inert atmosphere View Scheme