triethylamine in dichloromethane T=0 - 5°C; 2 h;

1: hydrogen / rhodium-platinium / acetic acid / 4 h / 36775.4 Torr 2: CrO3, conc. H2SO4 / H2O; acetone / 5 h / Ambient temperature 3: 78 percent / sodium methoxide / methanol / 4 h / Heating 4: 84 percent / bromine / methanol / 4 h / Ambient temperature 5: 66 percent / KOH / methanol / 1 h / 10 °C / other reagents; other temp.; other reaction time 6: 81 percent / triethylamine / CH2Cl2 / 2 h / 0 - 5 °C View Scheme

in diethyl ether 1 h; Ambient temperature;

1: thionyl chloride / 2 h / Heating 2: diethyl ether / 1 h 3: 77 percent / diethyl ether / 1 h / Ambient temperature View Scheme

1: CrO3, conc. H2SO4 / H2O; acetone / 5 h / Ambient temperature 2: 78 percent / sodium methoxide / methanol / 4 h / Heating 3: 84 percent / bromine / methanol / 4 h / Ambient temperature 4: 66 percent / KOH / methanol / 1 h / 10 °C / other reagents; other temp.; other reaction time 5: 81 percent / triethylamine / CH2Cl2 / 2 h / 0 - 5 °C View Scheme

1: 66 percent / KOH / methanol / 1 h / 10 °C / other reagents; other temp.; other reaction time 2: 81 percent / triethylamine / CH2Cl2 / 2 h / 0 - 5 °C View Scheme

1: 78 percent / sodium methoxide / methanol / 4 h / Heating 2: 84 percent / bromine / methanol / 4 h / Ambient temperature 3: 66 percent / KOH / methanol / 1 h / 10 °C / other reagents; other temp.; other reaction time 4: 81 percent / triethylamine / CH2Cl2 / 2 h / 0 - 5 °C View Scheme

1: 84 percent / bromine / methanol / 4 h / Ambient temperature 2: 66 percent / KOH / methanol / 1 h / 10 °C / other reagents; other temp.; other reaction time 3: 81 percent / triethylamine / CH2Cl2 / 2 h / 0 - 5 °C View Scheme

1: diethyl ether / 1 h 2: 77 percent / diethyl ether / 1 h / Ambient temperature View Scheme