carbon tetrabromide; triphenylphosphine in dichloromethane

1: 3-bromo-furan With n-butyllithium in tetrahydrofuran T=-78°C; 1 h; 2: oxirane With boron trifluoride diethyl etherate in tetrahydrofuran T=-78°C; 5 h;

lithium bromide in acetone 12 h; Heating; Yield given;

1.1: Mg / diethyl ether / 1 h / Heating; ultrasonication 1.2: diethyl ether / 0.5 h / 20 °C 1.3: p-TsOH; H2SO4 / diethyl ether / 0.17 h / 20 °C 2.1: 9-BBN / tetrahydrofuran; pentane / 1 h / Heating 2.2: NaOH (6N); H2O2 (30percent) / 1 h / 35 °C 3.1: 70 percent / CBr4; PPh3 / tetrahydrofuran / 0.92 h / 20 °C View Scheme

1.1: 9-BBN / tetrahydrofuran; pentane / 1 h / Heating 1.2: NaOH (6N); H2O2 (30percent) / 1 h / 35 °C 2.1: 70 percent / CBr4; PPh3 / tetrahydrofuran / 0.92 h / 20 °C View Scheme

1: 97 percent / dimethylsulfoxide 2: 80 percent / KOH / methanol / Heating 3: 97 percent / LiAlH4 / diethyl ether 4: 76 percent / CBr4, PPh3 / CH2Cl2 View Scheme

1: 97 percent / LiAlH4 / diethyl ether 2: 76 percent / CBr4, PPh3 / CH2Cl2 View Scheme

1: 80 percent / KOH / methanol / Heating 2: 97 percent / LiAlH4 / diethyl ether 3: 76 percent / CBr4, PPh3 / CH2Cl2 View Scheme

1: 2-(3-furyl)ethyl bromide With magnesium in tetrahydrofuran 2.5 h; 2: chloro-trimethyl-silane; cyclohexenon With copper(l) iodide; N,N,N',N,-tetramethylethylenediamine; triethylamine in tetrahydrofuran T=-78 - 20°C; 5 h;