N-chloro-succinimide; dimethylsulfide; triethylamine in toluene 1.) -30+/-5 deg C, 30 min; 4 h, -25 deg C, 2.) RT;

1: 86 percent / thionyl chloride / methanol / 6 h / Heating 2: 88 percent / lithium aluminum hydride / diethyl ether / 5 h / Heating 3: 1.) N-chlorosuccinimide, dimethyl sulfide, 2.) triethylamine / 1.) tolueene, - 25 deg C, 2.5 h, 2.) -25 deg C -> 25 deg C; other reagents View Scheme

2: 86 percent / thionyl chloride / methanol / 6 h / Heating 3: 88 percent / lithium aluminum hydride / diethyl ether / 5 h / Heating 4: 1.) N-chlorosuccinimide, dimethyl sulfide, 2.) triethylamine / 1.) tolueene, - 25 deg C, 2.5 h, 2.) -25 deg C -> 25 deg C; other reagents View Scheme

1: 88 percent / lithium aluminum hydride / diethyl ether / 5 h / Heating 2: 1.) N-chlorosuccinimide, dimethyl sulfide, 2.) triethylamine / 1.) tolueene, - 25 deg C, 2.5 h, 2.) -25 deg C -> 25 deg C; other reagents View Scheme

1: NaBr, Br2 / 1.) acetic acid, water, 0 deg C, 2 h, 2.) 100 deg C, 2.5 h 2: trimethyl borate, BH3*Me2S / tetrahydrofuran / 2.5 h / Heating 3: 89 percent / 1.) N-chlorosuccinimide, dimethyl sulfide, 2.) triethylamine / toluene / 1.) -30+/-5 deg C, 30 min; 4 h, -25 deg C, 2.) RT View Scheme

1: 1,8-dibromo-naphthalene With n-butyllithium 2: N,N-dimethyl-formamide

1: 94 percent / hydrochloric acid / aq. ethanol 2: 1.) sodium hydride / 1.) dichloromethane, 2.) chlorobenzene, 120 deg C, 0.5 h 3: lithium aluminum hydride / diethyl ether / Ambient temperature View Scheme