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: NaNO2/4.7percent aq. HBr 6: CuBr/concd. HBr / 1.) room temp., 20 min; 2.) 95 deg C, 5 min 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: NaNO2/4.7percent aq. HBr 4: CuBr/concd. HBr / 1.) room temp., 20 min; 2.) 95 deg C, 5 min 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: NaNO2/4.7percent aq. HBr 5: CuBr/concd. HBr / 1.) room temp., 20 min; 2.) 95 deg C, 5 min View Scheme

1: 77.6 percent / TiCl3 / tetrahydrofuran / 0.33 h / Ambient temperature 2: NaNO2/4.7percent aq. HBr 3: CuBr/concd. HBr / 1.) room temp., 20 min; 2.) 95 deg C, 5 min View Scheme

1: NaNO2/4.7percent aq. HBr 2: CuBr/concd. HBr / 1.) room temp., 20 min; 2.) 95 deg C, 5 min View Scheme