Multi-step reaction with 8 steps
1: 79.3 percent / Br2 / CS2 / 50 °C
2: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, 2 h
3: 1.) NaOEt, 2.) H2SO4 / 1.) EtOH, reflux, 3 h, 2.) EtOH, reflux, 1 h
4: 93 percent / Pd(OAc)2, PPh3, aq. K2CO3 / tetrahydrofuran; 1,2-dimethoxy-ethane / 5 h / Heating
5: 76 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Heating
6: CBr4, PPh3 / CH2Cl2 / 0.75 h / 0 °C
7: 73 percent / K2CO3 / dimethylformamide / 3 h / Heating
8: 75 percent / NaBH4 / tetrahydrofuran / 1 h / Ambient temperature
With
palladium diacetate; sodium tetrahydroborate; lithium aluminium tetrahydride; carbon tetrabromide; sulfuric acid; bromine; sodium ethanolate; sodium hydride; potassium carbonate; triphenylphosphine;
In
tetrahydrofuran; carbon disulfide; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0968-0896(96)00244-1