water in acetone T=70°C; 0.25 h;

sodium hydroxide 1 h; Heating;

trifluoroacetic acid 5 h; Ambient temperature;

1.1: CH2Cl2 / 5 h / -78 °C 1.2: 71 percent / DBU / CH2Cl2 / 5 h / 20 °C 2.1: 95 percent / sodium hydroxide / 1 h / Heating 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 10: 86 percent / diethyl ether / 3 h / 0 °C 11: CDCl3 / 3 h / 55 °C 12: methanol 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 11: 86 percent / diethyl ether / 3 h / 0 °C 12: CDCl3 / 3 h / 55 °C 13: methanol 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 8: 86 percent / diethyl ether / 3 h / 0 °C 9: CDCl3 / 3 h / 55 °C 10: methanol View Scheme

1: 90 percent / bromine / acetic acid / 3 h / Ambient temperature 2: 22 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene 3: 92 percent / boron tribromide / hexane; CH2Cl2 / 0.5 h / Heating 4: 90 percent / sodium ethoxide / ethanol / 0.5 h / Ambient temperature 5: 89 percent / acetic anhydride / dimethylsulfoxide / 0.25 h / 100 °C 6: 95 percent / aq. sodium hydroxide / 0.08 h 7: 86 percent / diethyl ether / 3 h / 0 °C 8: CDCl3 / 3 h / 55 °C 9: methanol View Scheme

1: 22 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene 2: 92 percent / boron tribromide / hexane; CH2Cl2 / 0.5 h / Heating 3: 90 percent / sodium ethoxide / ethanol / 0.5 h / Ambient temperature 4: 89 percent / acetic anhydride / dimethylsulfoxide / 0.25 h / 100 °C 5: 95 percent / aq. sodium hydroxide / 0.08 h 6: 86 percent / diethyl ether / 3 h / 0 °C 7: CDCl3 / 3 h / 55 °C 8: methanol View Scheme

1: 91 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / dimethylformamide / 3 h / -15 °C 2: 82 percent / diethyl ether / 0.25 h / 0 °C 3: 90 percent / bromine / acetic acid / 3 h / Ambient temperature 4: 22 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene 5: 92 percent / boron tribromide / hexane; CH2Cl2 / 0.5 h / Heating 6: 90 percent / sodium ethoxide / ethanol / 0.5 h / Ambient temperature 7: 89 percent / acetic anhydride / dimethylsulfoxide / 0.25 h / 100 °C 8: 95 percent / aq. sodium hydroxide / 0.08 h 9: 86 percent / diethyl ether / 3 h / 0 °C 10: CDCl3 / 3 h / 55 °C 11: methanol View Scheme