in xylene 26 h; Heatingin bromobenzene, reflux;

1: phosphorus tribromide 2: SOCl2 3: 1.) butyllithium, 2.) ZnBr2 / 3.) tetrakistriphenylphosphinepalladium(0) / 1.) THF, -78 deg C, 2.) THF, -20 deg C, 1 h, 3.) THF, RT, 16 h 4: 67 percent / xylene / 26 h / Heating; in bromobenzene, reflux View Scheme

1: 1.) phosphorus tribromide / 1.) CHCl3, 0 deg C, 1 h, 2.) CHCl3, reflux, 1 h 2: 1.) Mg, 3.) thionyl chloride / 1.) THF, 2.) THF, 1 h, 3.) 0 deg C, 1 h 3: 1.) Zn powder, 2.) butyl-lithium / 3.) <Pd(PPh3)4> / 1.) 1,2-dibromoethane, THF, reflux, 3.5 h, 2.) -78 deg C, -20 deg C, 1 h, 3.) THF, RT, 16 h 4: 67 percent / xylene / 26 h / Heating View Scheme

phenyllithium

1: aq. HBr, H2SO4 2: PhLi View Scheme

1: HCl 2: LiAlH4 3: aq. HBr, H2SO4 4: PhLi View Scheme

1: LiAlH4 2: aq. HBr, H2SO4 3: PhLi View Scheme