Multi-step reaction with 7 steps
1: 90 percent / O3, AcOH / CH2Cl2 / 0.42 h / -78 °C
2: 95 percent / p-toluenesulfonic acid / toluene / 12 h / Heating
3: 1.) n-BuLi, tetramethylethylenediamine, 2.) I2 / 1.) THF, hexane, a) -78 deg C, 15 min, b) -25 deg C, 45 min, 2.) THF, hexane, a) -78 deg C, 15 min, b) -25 deg C, 3 h
4: 60 percent / BBr3 / CH2Cl2 / 10 h / Ambient temperature
5: 98 percent / HCl / methanol / 6 h / Heating
6: 91 percent / pyridine / 25 h / Ambient temperature
7: 75 percent / K2CO3, Pd(PPh3)4 / toluene; ethanol / 2 h / 110 °C
With
pyridine; hydrogenchloride; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; N,N,N,N,-tetramethylethylenediamine; iodine; boron tribromide; potassium carbonate; toluene-4-sulfonic acid; ozone; acetic acid;
In
methanol; ethanol; dichloromethane; toluene;
DOI:10.1002/jhet.5570330670