1: 100 percent / diethyl ether / 12 h / 0 °C 2: 80 percent / 48percent hydrobromic acid / diethyl ether / 0.5 h / 0 °C 3: benzene / 0 - 5 °C 4: LiAlH4 / tetrahydrofuran; diethyl ether / 4 h / Heating View Scheme

1: 80 percent / SOCl2 2: 100 percent / diethyl ether / 12 h / 0 °C 3: 80 percent / 48percent hydrobromic acid / diethyl ether / 0.5 h / 0 °C 4: benzene / 0 - 5 °C 5: LiAlH4 / tetrahydrofuran; diethyl ether / 4 h / Heating View Scheme