sodium methylate in methanol T=40 - 50°C; 0.166667 h;

sodium ethanolate in ethanol

1: 65 percent / diethyl ether / Ambient temperature; overnight 2: 98 percent / triethylamine / tetrahydrofuran / 0.5 h / 25 °C 3: 73 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / dimethylformamide / 2 h / -15 °C 4: 97 percent / diethyl ether / 0.5 h / 0 °C 5: 54 percent / bromine / acetic acid / 2 h / Ambient temperature 6: 20 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene / 0.75 h 7: 1) boron tribromide, 2) conc. aq. hydrochloric acid / 1) dichloromethane, reflux, 30 min, 2) 30 min 8: 82 percent / sodium methoxide / methanol / 0.5 h View Scheme

1: 98 percent / triethylamine / tetrahydrofuran / 0.5 h / 25 °C 2: 73 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / dimethylformamide / 2 h / -15 °C 3: 97 percent / diethyl ether / 0.5 h / 0 °C 4: 54 percent / bromine / acetic acid / 2 h / Ambient temperature 5: 20 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene / 0.75 h 6: 1) boron tribromide, 2) conc. aq. hydrochloric acid / 1) dichloromethane, reflux, 30 min, 2) 30 min 7: 82 percent / sodium methoxide / methanol / 0.5 h View Scheme

1: 97 percent / diethyl ether / 0.5 h / 0 °C 2: 54 percent / bromine / acetic acid / 2 h / Ambient temperature 3: 20 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene / 0.75 h 4: 1) boron tribromide, 2) conc. aq. hydrochloric acid / 1) dichloromethane, reflux, 30 min, 2) 30 min 5: 82 percent / sodium methoxide / methanol / 0.5 h View Scheme

1: 54 percent / bromine / acetic acid / 2 h / Ambient temperature 2: 20 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene / 0.75 h 3: 1) boron tribromide, 2) conc. aq. hydrochloric acid / 1) dichloromethane, reflux, 30 min, 2) 30 min 4: 82 percent / sodium methoxide / methanol / 0.5 h View Scheme

1: 73 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / dimethylformamide / 2 h / -15 °C 2: 97 percent / diethyl ether / 0.5 h / 0 °C 3: 54 percent / bromine / acetic acid / 2 h / Ambient temperature 4: 20 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene / 0.75 h 5: 1) boron tribromide, 2) conc. aq. hydrochloric acid / 1) dichloromethane, reflux, 30 min, 2) 30 min 6: 82 percent / sodium methoxide / methanol / 0.5 h View Scheme

1: 20 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene / 0.75 h 2: 1) boron tribromide, 2) conc. aq. hydrochloric acid / 1) dichloromethane, reflux, 30 min, 2) 30 min 3: 82 percent / sodium methoxide / methanol / 0.5 h View Scheme

1: boron tribromide / CH2Cl2 / 0.5 h / Heating 2: sodium ethoxide / ethanol View Scheme

1: 64 percent / conc. HCl / acetic acid / 1.) 0.5 h, 90 deg C; 2.) 1.5 h, 60 deg C 2: 73 percent / sodium methoxide / methanol / 0.17 h / 40 - 50 °C View Scheme