1: 1.) N-chlorosuccinimide, dimethyl sulfide; 3.) triethylamine / 1.) toluene, 0 deg C, 20 min; 2.) toluene, -25 deg C, 2.7 h 3.) r.t., 15 min 2: 89 percent / sodium peroxydisulfate; disodium hydrogenphosphate / acetone; H2O / 0.67 h / Heating 3: 93 percent / m-chloroperbenzoic acid / ethyl acetate / 2 h / 35 °C View Scheme

With  hydrogenchloride; hydrogen; palladium on activated charcoal in  toluene T=40°C; 12 h;