sodium hydroxide in methanol 2 h; Heating;

1: 82.5 percent / H2O; aq. acetic acid / 12 h / Ambient temperature 2: 55.9 percent / H2O; dimethylformamide / 1.5 h / Heating 3: 86.2 percent / 50percent NaH / dimethylformamide; benzene / 1.) room temp., 15 min; 2.) room temp., 10 h 4: 77.6 percent / TiCl3 / tetrahydrofuran / 0.33 h / Ambient temperature 5: 1.) NaNO2/2 N HCl, 2.) aq. NaBF4 / 1.) H2O/THF, room temp., 20 min; 2.) H2O/THF, room temp., 30 min 6: 40.2 percent / 0.08 h / 187 °C View Scheme

1: 86.2 percent / 50percent NaH / dimethylformamide; benzene / 1.) room temp., 15 min; 2.) room temp., 10 h 2: 77.6 percent / TiCl3 / tetrahydrofuran / 0.33 h / Ambient temperature 3: 1.) NaNO2/2 N HCl, 2.) aq. NaBF4 / 1.) H2O/THF, room temp., 20 min; 2.) H2O/THF, room temp., 30 min 4: 40.2 percent / 0.08 h / 187 °C View Scheme

1: 55.9 percent / H2O; dimethylformamide / 1.5 h / Heating 2: 86.2 percent / 50percent NaH / dimethylformamide; benzene / 1.) room temp., 15 min; 2.) room temp., 10 h 3: 77.6 percent / TiCl3 / tetrahydrofuran / 0.33 h / Ambient temperature 4: 1.) NaNO2/2 N HCl, 2.) aq. NaBF4 / 1.) H2O/THF, room temp., 20 min; 2.) H2O/THF, room temp., 30 min 5: 40.2 percent / 0.08 h / 187 °C View Scheme

1: 77.6 percent / TiCl3 / tetrahydrofuran / 0.33 h / Ambient temperature 2: 1.) NaNO2/2 N HCl, 2.) aq. NaBF4 / 1.) H2O/THF, room temp., 20 min; 2.) H2O/THF, room temp., 30 min 3: 40.2 percent / 0.08 h / 187 °C View Scheme

1: 1.) NaNO2/2 N HCl, 2.) aq. NaBF4 / 1.) H2O/THF, room temp., 20 min; 2.) H2O/THF, room temp., 30 min 2: 40.2 percent / 0.08 h / 187 °C View Scheme