1: 80 percent / AlCl3 / nitromethane; H2O / 0.5 h / 60 °C 2: 84 percent / TsOH / toluene; various solvent(s) / 11 h / 80 °C 3: n-BuLi / tetrahydrofuran / 1 h / -78 °C 4: HCl / methanol / 2 h / 20 °C 5: 65 percent / I2 / dimethylsulfoxide / 5 h / 110 °C 6: 88 percent / Pd(OAc)2 / triethylamine; acetonitrile / 7.5 h / 50 °C 7: 40 percent / 2,6-di-t-butyl-4-methylphenol; air / toluene / 24 h / 200 °C 8: 74 percent / AlCl3 / toluene / 2 h / 110 °C View Scheme

<b>Multi-step reaction with 3 steps<br /> </b>1.1: 94 percent / K₂CO₃ / acetone / 9.5 h / 50 &deg;C<br />2.1: mCPBA / CH₂Cl₂ / 11 h / Heating<br />2.2: 81 percent / Et₃N / methanol / 2 h / 20 &deg;C<br />3.1: 74 percent / DBU / 72 h / 75 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1.1: 95 percent / bromine / acetic acid / 6 h / 20 &deg;C<br />2.1: 94 percent / K₂CO₃ / acetone / 9.5 h / 50 &deg;C<br />3.1: mCPBA / CH₂Cl₂ / 11 h / Heating<br />3.2: 81 percent / Et₃N / methanol / 2 h / 20 &deg;C<br />4.1: 74 percent / DBU / 72 h / 75 &deg;C<br /> <br /> &nbsp;