in water; N,N-dimethyl-formamide 1.5 h; Heating;

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 6: 53.6 percent / 40percent aq. NaOH / methanol / 2 h / Heating 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: NaNO2/2 N HCl 5: CuCl/concd. HCl / 1.) room temp., 0.5 h; 2.) 95 deg C, 5 min 6: 78.1 percent / 40percent aq. NaOH / methanol / 2 h / Heating 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 6: 93.9 percent / 40percent aq. NaOH / methanol / 2 h / Heating View Scheme

acetic acid 4.5 h;

in water; acetic acid 12 h; Ambient temperature;

sodium tetrahydroborate; dimethylammonium chloride in water 2.5 h; Ambient temperature;

sodium tetrahydroborate in water T=13 - 18°C; 2.5 h;

in acetic acid

1: p-toluenesulfonic acid 2: EtOK, (COOEt)2 / dimethylsulfoxide; dimethylformamide / 2 h / Ambient temperature 3: 24 percent / acetonitrile View Scheme