aluminium trichloride in benzene 1 h; Ambient temperature;

1: 56 percent / AlCl3 / benzene / 1 h / Ambient temperature 2: 1.) n-butyllithium / 1.) THF, 1 h, 2.) 25 min 3: 36 percent / PBr3 / benzene / 2.5 h / 75 °C 4: 1.) ethylmagnesium bromide / 1.) THF, ether, reflux, 3 h, 2.) reflux 5: 1.) methanesulfonic acid / 2.) 10 percent Pd/C / 1.) CHCl3, r.t., 2.) triglyme, reflux View Scheme