Multi-step reaction with 12 steps
1: TiCl4 / CH2Cl2 / 1 h / 25 °C
2: 89 percent / KOH, NaBH3CN / methanol / 2.5 h / 25 °C
3: 96 percent / CH2Cl2 / 3 h / 25 °C
4: 94 percent / Na, Fe(NO3)*9H2O / liquid ammonia / 4 h
5: 58 percent / NBS / benzene / 20 h / 25 °C
6: 86 percent / BBr3 / CH2Cl2 / 1.) -78 deg C, 2 h; 2.) 25 deg C, 2 h
7: 78 percent / K2CO3, NaI / acetone / 5 h / Heating
8: 77 percent / NH4OAc / acetic acid / 1.5 h / Heating
9: 48 percent / Cu(NO3)2*3H2O / acetic anhydride / 1 h / 65 °C
10: 92 percent / Fe, AcOH, silica gel / toluene / 1 h / Heating
11: H2O; ethanol; acetic acid / 8 h / 25 °C
12: ethanol; ethyl acetate / 12 h
With
potassium hydroxide; N-Bromosuccinimide; Fe(NO3)*9H2O; ammonium acetate; sodium; silica gel; boron tribromide; titanium tetrachloride; iron; sodium cyanoborohydride; potassium carbonate; copper(II) nitrate; acetic acid; sodium iodide;
In
methanol; ethanol; dichloromethane; ammonia; water; acetic anhydride; acetic acid; ethyl acetate; acetone; toluene; benzene;
DOI:10.1021/ja00311a065