boron tribromide in dichloromethane T=0°C; 2 h;

1: in dichloromethane T=-78°C; 5 h; 2: With 1,8-diazabicyclo[5.4.0]undec-7-ene in dichloromethane T=20°C; 5 h;

sodium hydroxide 0.0833333 h;

1: 72 percent / toluene / 3 h / 95 °C 2: 1.) lithium di-isopropylamide / 1.) -78 deg C, 25 min, 2.) room temperature, 18 h View Scheme

1: 90 percent / sodium ethoxide / ethanol / 0.5 h / Ambient temperature 2: 89 percent / acetic anhydride / dimethylsulfoxide / 0.25 h / 100 °C 3: 95 percent / aq. sodium hydroxide / 0.08 h View Scheme

1: 68 percent / triethylamine / tetrahydrofuran / 0.5 h / 25 °C 2: 91 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / dimethylformamide / 3 h / -15 °C 3: 82 percent / diethyl ether / 0.25 h / 0 °C 4: 90 percent / bromine / acetic acid / 3 h / Ambient temperature 5: 22 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene 6: 92 percent / boron tribromide / hexane; CH2Cl2 / 0.5 h / Heating 7: 90 percent / sodium ethoxide / ethanol / 0.5 h / Ambient temperature 8: 89 percent / acetic anhydride / dimethylsulfoxide / 0.25 h / 100 °C 9: 95 percent / aq. sodium hydroxide / 0.08 h View Scheme

1: 89 percent / acetic anhydride / dimethylsulfoxide / 0.25 h / 100 °C 2: 95 percent / aq. sodium hydroxide / 0.08 h View Scheme

1: 99 percent / zinc iodide / 0.25 h / 0 °C 2: 2) dil. aq. hydrochloric acid / 1) diethyl ether, reflux, 3 h, 2) 25 deg C, overnight 3: 68 percent / triethylamine / tetrahydrofuran / 0.5 h / 25 °C 4: 91 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / dimethylformamide / 3 h / -15 °C 5: 82 percent / diethyl ether / 0.25 h / 0 °C 6: 90 percent / bromine / acetic acid / 3 h / Ambient temperature 7: 22 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene 8: 92 percent / boron tribromide / hexane; CH2Cl2 / 0.5 h / Heating 9: 90 percent / sodium ethoxide / ethanol / 0.5 h / Ambient temperature 10: 89 percent / acetic anhydride / dimethylsulfoxide / 0.25 h / 100 °C 11: 95 percent / aq. sodium hydroxide / 0.08 h View Scheme

1: 2) dil. aq. hydrochloric acid / 1) diethyl ether, reflux, 3 h, 2) 25 deg C, overnight 2: 68 percent / triethylamine / tetrahydrofuran / 0.5 h / 25 °C 3: 91 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / dimethylformamide / 3 h / -15 °C 4: 82 percent / diethyl ether / 0.25 h / 0 °C 5: 90 percent / bromine / acetic acid / 3 h / Ambient temperature 6: 22 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene 7: 92 percent / boron tribromide / hexane; CH2Cl2 / 0.5 h / Heating 8: 90 percent / sodium ethoxide / ethanol / 0.5 h / Ambient temperature 9: 89 percent / acetic anhydride / dimethylsulfoxide / 0.25 h / 100 °C 10: 95 percent / aq. sodium hydroxide / 0.08 h View Scheme

1: 82 percent / diethyl ether / 0.25 h / 0 °C 2: 90 percent / bromine / acetic acid / 3 h / Ambient temperature 3: 22 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene 4: 92 percent / boron tribromide / hexane; CH2Cl2 / 0.5 h / Heating 5: 90 percent / sodium ethoxide / ethanol / 0.5 h / Ambient temperature 6: 89 percent / acetic anhydride / dimethylsulfoxide / 0.25 h / 100 °C 7: 95 percent / aq. sodium hydroxide / 0.08 h View Scheme