1: 73 percent / potassium permanganate, sodium hydrogen carbonate / H2O / 4 h / Heating 2: 91 percent / BF3 / 12 h 3: 91 percent / hydrogen / 10percent Pd/C / CH2Cl2; ethanol / 12 h 4: 20percent H2SO4, sodium nitrite / H2O / 0 °C 5: KI / H2O / 2 h / 50 °C 6: 97 percent / Et3N, Pd(OAc)2, P(o-Tol)3 / dimethylformamide / 3 h / 100 °C 7: KOH / ethanol / 3 h / Heating View Scheme

1: 91 percent / BF3 / 12 h 2: 91 percent / hydrogen / 10percent Pd/C / CH2Cl2; ethanol / 12 h 3: 20percent H2SO4, sodium nitrite / H2O / 0 °C 4: KI / H2O / 2 h / 50 °C 5: 97 percent / Et3N, Pd(OAc)2, P(o-Tol)3 / dimethylformamide / 3 h / 100 °C 6: KOH / ethanol / 3 h / Heating View Scheme

1: 91 percent / hydrogen / 10percent Pd/C / CH2Cl2; ethanol / 12 h 2: 20percent H2SO4, sodium nitrite / H2O / 0 °C 3: KI / H2O / 2 h / 50 °C 4: 97 percent / Et3N, Pd(OAc)2, P(o-Tol)3 / dimethylformamide / 3 h / 100 °C 5: KOH / ethanol / 3 h / Heating View Scheme

1: 68 percent / 1.) n-BuLi; 2.) triisopropyl borate, aq. HCl / 1.) hexane, Et2O, -78 deg C, 30 min; 2.) hexane, Et2O, -78 deg C, 30 min, then room temp. 2: 97 percent / Et3N, Pd(OAc)2, P(o-Tol)3 / dimethylformamide / 3 h / 100 °C 3: KOH / ethanol / 3 h / Heating View Scheme

1: 97 percent / Et3N, Pd(OAc)2, P(o-Tol)3 / dimethylformamide / 3 h / 100 °C 2: KOH / ethanol / 3 h / Heating View Scheme

1: 20percent H2SO4, sodium nitrite / H2O / 0 °C 2: KI / H2O / 2 h / 50 °C 3: 97 percent / Et3N, Pd(OAc)2, P(o-Tol)3 / dimethylformamide / 3 h / 100 °C 4: KOH / ethanol / 3 h / Heating View Scheme

1: 97 percent / Et3N, Pd(OAc)2, P(o-Tol)3 / dimethylformamide / 3 h / 100 °C 2: KOH / ethanol / 3 h / Heating View Scheme