sodium hydride 1.) DMSO, 0 deg C, 5 min, 2.) THF, room temp., 36 h, 3.) 9-anthraldehyde, room temp., 6 d, 4.) aq. HCl;

1: 19 percent / NaH / 1.) DMSO, 0 deg C, 10 min, 2.) THF, room temp., 4 d, 3.) aq. HCl 2: 75 percent / toluene / 30 h / Heating 3: 58 percent / NaOC2H5 / dimethylformamide / 24 h / Ambient temperature View Scheme

1: 75 percent / toluene / 30 h / Heating 2: 58 percent / NaOC2H5 / dimethylformamide / 24 h / Ambient temperature View Scheme

Substitution;