Multi-step reaction with 11 steps
1: 91 percent / bromine / CH2Cl2 / 0.25 h / 0 °C
2: 66 percent / polyphosphoric acid / 1 h / 60 °C
3: 1.) BF3*Et2O, 2.) ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, -78 to -15 deg C, 2 h
4: 1.) LiHMDS / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2.5 h
5: 91 percent / NaOAc*3H2O, H2 / 10 percent Pd/C / ethanol / 3040 Torr
6: 6.0 M aq. HCl / tetrahydrofuran / 2.5 h / 25 °C
7: aq. AgNO3, aq. KOH / ethanol / 0.5 h
8: 96 percent H2SO4 / 2 h / Heating
9: 1.) trimethylaluminium / 1.) toluene, 1 h, 2.) toluene, reflux, 2.5 h
10: p-TsOH / xylene / 48 h / Heating
11: BH3*THF / tetrahydrofuran / 4 h / Heating
With
hydrogenchloride; potassium hydroxide; PPA; borane-THF; sulfuric acid; boron trifluoride diethyl etherate; hydrogen; bromine; trimethylaluminum; sodium acetate; toluene-4-sulfonic acid; silver nitrate; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; dichloromethane; xylene;