1: 96 percent / NaBH4 / tetrahydrofuran; methanol / 2 h 2: SOCl2 / benzene / 20 °C 3: dimethylsulfoxide; benzene / 2 h 4: 89 percent / 4N NaOH / ethanol / 20 h / Heating 5: SOCl2 / benzene / 2 h / 50 - 60 °C 6: 86 percent / benzene; pyridine / 20 °C 7: 83 percent / POCl3 / toluene / 3 h / Heating 8: 97 percent / NaBH4 / methanol / 0.25 h 9: 82 percent / Pd(OAc)2; PPh3; K2CO3 / toluene / 18 h / Heating 10: 86 percent / LiAlH4 / tetrahydrofuran / 0.75 h / Heating View Scheme

potassium fluoride in N,N-dimethyl-formamide T=115°C; 2 h;

sodium tungstate; hydrogen bromide; dihydrogen peroxide in acetic acid T=40 - 45°C; 0.5 h;

1: 70 percent / Br2 / acetic acid / 1.5 h / 20 - 25 °C 2: 96 percent / AlCl3 / CH2Cl2; pyridine / 30 h / Heating 3: 86 percent / KF / dimethylformamide / 2 h / 115 °C View Scheme

1: 96 percent / AlCl3 / CH2Cl2; pyridine / 30 h / Heating 2: 86 percent / KF / dimethylformamide / 2 h / 115 °C View Scheme

Yield given. Multistep reaction;

1: toluene / 3 h / Heating 2: 92 percent / sodium borohydride / methanol / 0.5 h / 20 °C 3: 73 percent / NaOH / diethyl ether; H2O / 0.5 h / 0 °C 4: 63 percent / n-BuLi / hexane; tetrahydrofuran / 0.83 h / -90 - -40 °C 5: 91 percent / anisole; trifluoroacetic acid / 24 h / Heating View Scheme