1: 1.) POCl3 / 1.) 0 deg C, 15 min, 2.) 60 deg C, 10 h 2: 78.6 percent / NaBH4 / propan-2-ol 3: 25 g / HBr(g) / benzene; petroleum ether / -15 °C 4: NaI / acetone / 72 h / Ambient temperature View Scheme

1: 25 g / HBr(g) / benzene; petroleum ether / -15 °C 2: NaI / acetone / 72 h / Ambient temperature View Scheme

1: 78.6 percent / NaBH4 / propan-2-ol 2: 25 g / HBr(g) / benzene; petroleum ether / -15 °C 3: NaI / acetone / 72 h / Ambient temperature View Scheme

1: 93 percent / aq. H2SO4 / 12 h / 140 °C 2: 1.) POCl3 / 1.) 0 deg C, 15 min, 2.) 60 deg C, 10 h 3: 78.6 percent / NaBH4 / propan-2-ol 4: 25 g / HBr(g) / benzene; petroleum ether / -15 °C 5: NaI / acetone / 72 h / Ambient temperature View Scheme

sodium iodide in acetone 72 h; Ambient temperature; Yield given;