sodium iodide in acetone 12 h; Heating;

1: 86 percent / HBr / 1 h / 100 - 110 °C 2: 1.) NaOEt / 1.) EtOH, 80 deg C, 10 min, 2.) EtOH, N,N-dimethylacetamide, from 80 deg C to 90 deg C, 5 h 3: aq. KOH / methanol / 8 h / 40 °C 4: 3 h / 150 - 170 °C 5: 91 percent / NaI / acetone / 12 h / Heating View Scheme

1: 89 percent / LiAlH4 / tetrahydrofuran / 2 h / -10 - 15 °C 2: 86 percent / HBr / 1 h / 100 - 110 °C 3: 1.) NaOEt / 1.) EtOH, 80 deg C, 10 min, 2.) EtOH, N,N-dimethylacetamide, from 80 deg C to 90 deg C, 5 h 4: aq. KOH / methanol / 8 h / 40 °C 5: 3 h / 150 - 170 °C 6: 91 percent / NaI / acetone / 12 h / Heating View Scheme