Multi-step reaction with 6 steps
1: 91 percent / p-TsOH*H2O / diethyl ether / 18 h / Heating
2: 1) BuLi, 2) iodine / 1) THF, -78 deg C, 30 min, 2) a) THF, -78 deg C, 10 min, b) to room temperature
3: 47 percent / dimethylformamide; hexamethylphosphoric acid triamide / 1.5 h / 60 °C
4: Br2, Fe powder / CCl4 / 2 h / 60 °C
5: 4-(dimethylamino)pyridine, triethylamine / tetrahydrofuran / 2 h / Ambient temperature
6: 1) a) Mg, 1,2-dibromomethane, c) ZnCl2 / 2) tetrakis(triphenylphosphine)palladium / 1) THF, a) 45 deg C, 10 min, b) ultrasonic bath, room temperature, 1 h, c) 25 deg C, 15 min, 2) room temperature, 1 h
With
dmap; n-butyllithium; 1,2-dibromomethane; bromine; iodine; iron; toluene-4-sulfonic acid; magnesium; triethylamine; zinc(II) chloride;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1021/jo00061a048