phosphorus tribromide in tetrahydrofuran; benzene 1.) 0 deg C, 2.) 20 deg C, 3.5 h;

1: 32 percent / potassium carbonate / acetone / 18 h / Heating 2: 89 percent / 1.) lithium aluminium hydride / diethyl ether / 1.) reflux, 3 h, 2.) 16 h 3: phosphorus tribromide / tetrahydrofuran; benzene / 1.) 0 deg C, 2.) 20 deg C, 3.5 h View Scheme

1: 89 percent / 1.) lithium aluminium hydride / diethyl ether / 1.) reflux, 3 h, 2.) 16 h 2: phosphorus tribromide / tetrahydrofuran; benzene / 1.) 0 deg C, 2.) 20 deg C, 3.5 h View Scheme

1: 61 percent / benzene / 6 h / Heating 2: 73 percent / 1.) n-butyl-lithium / tetrahydrofuran; hexane / 1.) 20 deg C, 90 min, 2.) 20 deg C, 18 h 3: 71 percent / pyridine / 22 h 4: 97 percent / H2 / 10percent palladium on carbon / ethyl acetate / 16 h / 20 °C 5: 24 percent / potassium carbonate, potassium iodide, 18-crown-6 / acetone / 22 h / Heating 6: H2 / Lindlar catalyst / ethyl acetate / 0.33 h / 20 °C 7: 40 mg / 1.25 h / 150 °C 8: 90 percent / aqueous 10percent sodium hydroxide, ethanol / 1 h / 85 °C View Scheme