thionyl chloride in dichloromethane 1.5 h; Heating;

1: 95 percent / BBr3 / CH2Cl2 2: 1.) KF; / 1.) DMF, room temperature, 2.5 h, 2.) 115 deg C, 1.5 h; 3: 86 percent / NaBH4 / propan-2-ol / 1 h / 70 °C 4: 89 percent / SOCl2 / CH2Cl2 / 1.5 h / Heating View Scheme

1: 86 percent / NaBH4 / propan-2-ol / 1 h / 70 °C 2: 89 percent / SOCl2 / CH2Cl2 / 1.5 h / Heating View Scheme