sulfuric acid; trichlorophosphate in benzene Heating;

1: 1.) KI / 1.) ethanol, 2.) ethanol, RT, 2 h 2: 60 percent / LiAlH4 / tetrahydrofuran / -10 °C View Scheme

1: 1.) KI / 1.) ethanol, 2.) ethanol, RT, 2 h 2: 60 percent / LiAlH4 / tetrahydrofuran / -10 °C 3: N-bromosuccinimide (NBS) / CHCl3 / 0.17 h / Ambient temperature 4: H2, Et3N / 10percent Pd/C / methanol / 0.33 h / Ambient temperature 5: 34 percent / H2O, N-bromosuccinimide (NBS) / CHCl3 / 3 h / Ambient temperature View Scheme

1: 1.) KI / 1.) ethanol, 2.) ethanol, RT, 2 h 2: 60 percent / LiAlH4 / tetrahydrofuran / -10 °C 3: N-bromosuccinimide (NBS) / CHCl3 / 0.17 h / Ambient temperature 4: 64 percent / H2 / 10percentPd/C / methanol / 24 h / Ambient temperature View Scheme

1: 1.) KI / 1.) ethanol, 2.) ethanol, RT, 2 h 2: 60 percent / LiAlH4 / tetrahydrofuran / -10 °C 3: N-bromosuccinimide (NBS) / CHCl3 / 0.17 h / Ambient temperature 4: H2, Et3N / 10percent Pd/C / methanol / 0.33 h / Ambient temperature View Scheme