hydrogen; palladium on activated charcoal in 1,4-dioxane; ethanol P=2327.2 Torr; 2 h;

boron tribromide in dichloromethane a) -78 deg C, 0.5 h, b) -78 to -20 deg C, 10 min;

1: 68.3 percent / NaOAc*3H2O, Na2S2O4 / H2O / 4 h / 70 °C 2: 60 percent / Cu, Cu2O, K2CO3 / bis-(2-methoxy-ethyl) ether / 5 h / Heating 3: SOCl2, pyridine / benzene / 0.17 h / 0 °C 4: 1.) piperidine, Et3N, 2.) POCl3 / 1.) CHCl3, RT, 20 min, 2.) 100 deg C, 30 min 5: 96 percent / K2CO3 / acetone / 16 h / Heating 6: 54 percent / BBr3 / CH2Cl2 / a) -78 deg C, 0.5 h, b) -78 to -20 deg C, 10 min View Scheme

1: 60 percent / Cu, Cu2O, K2CO3 / bis-(2-methoxy-ethyl) ether / 5 h / Heating 2: SOCl2, pyridine / benzene / 0.17 h / 0 °C 3: 1.) piperidine, Et3N, 2.) POCl3 / 1.) CHCl3, RT, 20 min, 2.) 100 deg C, 30 min 4: 96 percent / K2CO3 / acetone / 16 h / Heating 5: 54 percent / BBr3 / CH2Cl2 / a) -78 deg C, 0.5 h, b) -78 to -20 deg C, 10 min View Scheme

1: 96 percent / K2CO3 / acetone / 16 h / Heating 2: 54 percent / BBr3 / CH2Cl2 / a) -78 deg C, 0.5 h, b) -78 to -20 deg C, 10 min View Scheme

1: SOCl2, pyridine / benzene / 0.17 h / 0 °C 2: 1.) piperidine, Et3N, 2.) POCl3 / 1.) CHCl3, RT, 20 min, 2.) 100 deg C, 30 min 3: 96 percent / K2CO3 / acetone / 16 h / Heating 4: 54 percent / BBr3 / CH2Cl2 / a) -78 deg C, 0.5 h, b) -78 to -20 deg C, 10 min View Scheme