hydrogenchloride; water; acetic acid 12 h; Reflux; Overall yield = 98 percent;

1.1: thionyl chloride / 3 h / |Inert atmosphere; |Reflux 2.1: dichloromethane / 12 h / 0 - 20 °C / |Inert atmosphere 3.1: sec.-butyllithium; N,N,N',N,-tetramethylethylenediamine / tetrahydrofuran; cyclohexane / 2 h / -78 °C / |Inert atmosphere 3.2: -78 - 20 °C / |Inert atmosphere 4.1: hydrogenchloride; acetic acid; water / 12 h / |Reflux View Scheme

1.1: dichloromethane / 12 h / 0 - 20 °C / |Inert atmosphere 2.1: sec.-butyllithium; N,N,N',N,-tetramethylethylenediamine / tetrahydrofuran; cyclohexane / 2 h / -78 °C / |Inert atmosphere 2.2: -78 - 20 °C / |Inert atmosphere 3.1: hydrogenchloride; acetic acid; water / 12 h / |Reflux View Scheme

1.1: sec.-butyllithium; N,N,N',N,-tetramethylethylenediamine / tetrahydrofuran; cyclohexane / 2 h / -78 °C / |Inert atmosphere 1.2: -78 - 20 °C / |Inert atmosphere 2.1: hydrogenchloride; acetic acid; water / 12 h / |Reflux View Scheme

1: 1.) t-BuOK / 1.) t-BuOH, ether, 20 deg C, 30 min, 2.) t-BuOH, ether, THF, 3 h 2: 68 percent / AlCl3 / CH2Cl2 / 3 h / Ambient temperature View Scheme