1.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 0 °C 1.2: 90 percent / tetrahydrofuran; hexane / 0 - 20 °C 2.1: 68 percent / aq. HCO2H; Pd(OAc)2; Ph3P / dimethylformamide / 60 - 70 °C View Scheme

With  lithium diisopropyl amide in  tetrahydrofuran  0 deg C to rt, 3 h;   

Stage #1: 2-chloro-9-phenanthrol With  n-butyllithium in  tetrahydrofuran; hexane T=0°C; Metallation; Acylation; 0.0833333 h; Stage #2: trifluoromethylsulfonic anhydride  in  tetrahydrofuran; hexane T=0 - 20°C;