hydrogen; thiourea; palladium on barium sulfate in xylene

1: PCl5 / (heating) 2: H2, thiourea / Pd-BaSO4 / xylene View Scheme

1: 65 percent / H2SO4 / toluene / 1 h / Heating 2: 38 percent / aq NaOH / CHCl3 / 1.) RT, 2 h, 2.) reflux, 8 h 3: 1.) n-butyllithium / 1.) THF, -70 deg C, 45 min, 2a.) -70 deg C, 45 min, 2b.) RT, 12 h View Scheme

1: 38 percent / aq NaOH / CHCl3 / 1.) RT, 2 h, 2.) reflux, 8 h 2: 1.) n-butyllithium / 1.) THF, -70 deg C, 45 min, 2a.) -70 deg C, 45 min, 2b.) RT, 12 h View Scheme

1: 78 percent / N-bromosuccinimide, water / dimethylsulfoxide / 15 h 2: 65 percent / H2SO4 / toluene / 1 h / Heating 3: 38 percent / aq NaOH / CHCl3 / 1.) RT, 2 h, 2.) reflux, 8 h 4: 1.) n-butyllithium / 1.) THF, -70 deg C, 45 min, 2a.) -70 deg C, 45 min, 2b.) RT, 12 h View Scheme

n-butyllithium 1.) THF, -70 deg C, 45 min, 2a.) -70 deg C, 45 min, 2b.) RT, 12 h; Yield given. Multistep reaction;