Multi-step reaction with 5 steps
1: 1) n-butyllithium, TMEDA, 2) I2 / 1) THF, hexane, -10 deg C, 2 h, 2) THF, a) -70 deg C, 15 min., b) -10 deg C, 2 h
2: 80 percent / BBr3 / CH2Cl2 / a) -70 deg C, 15 min., b) room temperature, 15 h
3: 91 percent / pyridine / a) 0 deg C, 5 min, b) room temperature, 24 h
4: 75 percent / Na2CO3 / Pd(PPh3)4 / ethanol; toluene; H2O / 12 h / Heating
5: 74 percent / LiCl / Pd(PPh3)4 / dioxane / 15 h / Heating
With
pyridine; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; iodine; boron tribromide; sodium carbonate; lithium chloride;
tetrakis(triphenylphosphine) palladium(0);
In
1,4-dioxane; ethanol; dichloromethane; water; toluene;
DOI:10.1016/S0040-4020(01)92191-X