Multi-step reaction with 11 steps
1: 86 percent / aq. KOH / 50 °C
2: 73 percent / triphenylphosphine; NEt3; pyridine / CCl4; acetonitrile / 24 h / 27 - 30 °C
3: iodobenzene diacetate; 2,2,2-trifluoroethanol / 0.5 h / 20 °C
4: 0.48 g / pyridine; DMAP / 20 °C
5: 96 percent / H2; PtO2 / ethyl acetate / 20 °C / 760.05 Torr
6: 79 percent / K2CO3 / methanol
7: 97 percent / K2CO3 / acetone; dimethylformamide
8: 87 percent / BBr3 / CH2Cl2 / 1 h / -60 - 0 °C
9: 98 percent / Cs2CO3 / acetone / 2 h / 50 °C
10: LiAlH4 / tetrahydrofuran / 48 h / Heating
11: Et3N / dimethylsulfoxide; CH2Cl2 / -78 °C
With
pyridine; dmap; platinum(IV) oxide; potassium hydroxide; lithium aluminium tetrahydride; 2,2,2-trifluoroethanol; [bis(acetoxy)iodo]benzene; hydrogen; boron tribromide; potassium carbonate; caesium carbonate; triethylamine; triphenylphosphine;
In
tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1021/ja016030z