sodium tetrahydroborate in ethanol 20 h; Ambient temperature;

1: 0.75 h / 200 - 210 °C 2: 94 percent / HF / 90 h / Ambient temperature 3: 1.) sodium ethoxide / 1.) benzene, 1 h. 2.) benzene, 24 h 4: 1.) sodium ethoxide / 1.) benzene, 2 h, 2.) DMF, 100 deg C, 20 h 5: 48percent HBr, glacial acetic acid / 120 h / Heating 6: H2SO4 7: 27.6 percent / NH3 / methanol / 168 h / Ambient temperature 8: 51 percent / NaBH4 / ethanol / 20 h / Ambient temperature View Scheme

1: 1.) sodium ethoxide / 1.) benzene, 1 h. 2.) benzene, 24 h 2: 1.) sodium ethoxide / 1.) benzene, 2 h, 2.) DMF, 100 deg C, 20 h 3: 48percent HBr, glacial acetic acid / 120 h / Heating 4: H2SO4 5: 27.6 percent / NH3 / methanol / 168 h / Ambient temperature 6: 51 percent / NaBH4 / ethanol / 20 h / Ambient temperature View Scheme

1: 94 percent / HF / 90 h / Ambient temperature 2: 1.) sodium ethoxide / 1.) benzene, 1 h. 2.) benzene, 24 h 3: 1.) sodium ethoxide / 1.) benzene, 2 h, 2.) DMF, 100 deg C, 20 h 4: 48percent HBr, glacial acetic acid / 120 h / Heating 5: H2SO4 6: 27.6 percent / NH3 / methanol / 168 h / Ambient temperature 7: 51 percent / NaBH4 / ethanol / 20 h / Ambient temperature View Scheme

1: 27.6 percent / NH3 / methanol / 168 h / Ambient temperature 2: 51 percent / NaBH4 / ethanol / 20 h / Ambient temperature View Scheme

1: 48percent HBr, glacial acetic acid / 120 h / Heating 2: H2SO4 3: 27.6 percent / NH3 / methanol / 168 h / Ambient temperature 4: 51 percent / NaBH4 / ethanol / 20 h / Ambient temperature View Scheme

1: 1.) sodium ethoxide / 1.) benzene, 2 h, 2.) DMF, 100 deg C, 20 h 2: 48percent HBr, glacial acetic acid / 120 h / Heating 3: H2SO4 4: 27.6 percent / NH3 / methanol / 168 h / Ambient temperature 5: 51 percent / NaBH4 / ethanol / 20 h / Ambient temperature View Scheme