1: 74 percent / PBr3, pyridine / diethyl ether / 1a) overnight, 2) reflux, 2 h 2: 1) sodium / 1) benzene, DMF, 2) benzene, reflux, 12 h 3: 58 percent / NaCl / H2O; dimethylsulfoxide / 8 h / 180 °C View Scheme

(i) N-chloro-succinimide , Me2S, CH2Cl2, (ii) /BRN= 3928703/, THF; Multistep reaction;

1: 74 percent / PBr3, pyridine / diethyl ether / 1a) overnight, 2) reflux, 2 h 2: 1) sodium / 1) benzene, DMF, 2) benzene, reflux, 12 h 3: 58 percent / NaCl / H2O; dimethylsulfoxide / 8 h / 180 °C 4: 54 percent / lithium aluminium monoethoxy hydride / diethyl ether 5: 60 percent / pyridine / 48 h View Scheme

1: 74 percent / PBr3, pyridine / diethyl ether / 1a) overnight, 2) reflux, 2 h 2: 1) sodium / 1) benzene, DMF, 2) benzene, reflux, 12 h 3: 58 percent / NaCl / H2O; dimethylsulfoxide / 8 h / 180 °C 4: 54 percent / lithium aluminium monoethoxy hydride / diethyl ether View Scheme