diethyl ether

1: With n-butyllithium; diisopropylamine in tetrahydrofuran T=-78°C; 0.233333 h; Inert atmosphere; 2: With iodine in tetrahydrofuran T=-78°C; Overall yield = 75 percent;

1.1: acetic acid; sodium nitrite / dimethyl sulfoxide / 8 h / 40 °C / |Inert atmosphere 2.1: diethyl ether / 0 °C / |Inert atmosphere 3.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 0.23 h / -78 °C / |Inert atmosphere 3.2: -78 °C View Scheme

1.1: diethyl ether / 0 °C / |Inert atmosphere 2.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 0.23 h / -78 °C / |Inert atmosphere 2.2: -78 °C View Scheme

palladium diacetate; triethylamine; triphenylphosphine

palladium on activated charcoal

lithium cyclohexylisopropyl amide; iodine 1.) THF, -78 deg C, 10 min; Yield given. Yields of byproduct given. Title compound not separated from byproducts;