1: aqueous KOH; diethyl ether / 0 °C 2: iodine; sodium acetate; acetic acid; bromine 3: glacial acetic acid; sodium acetate; bromine View Scheme

1: iodine; sodium acetate; acetic acid; bromine 2: glacial acetic acid; sodium acetate; bromine View Scheme

sodium acetate

1.1: 95 percent / NaHCO3 / methanol / 3 h / Heating 2.1: 89 percent / K2CO3 / dimethylformamide / 12 h / 50 °C 3.1: n-BuLi / diethyl ether; hexane / 1 h / -78 °C 3.2: diethyl ether; hexane / 1 h / -78 °C 4.1: 88 percent / Na2CO3; O2 / Pd(OAc)2 / dimethylformamide / 12 h / 50 °C / 760 Torr 5.1: 90 percent / NBS; AIBN / CCl4 / 10 h / Heating 6.1: 99 percent / NaN3 / ethanol; H2O / 8 h / Heating 7.1: NaBH4; [4(S)-Ph-oxazolidin-2-ylidene][4(S)-Ph-2-oxazolin-2-yl](CN)C / CoCl2*6H2O / ethanol; dimethylformamide / 24 h / 25 °C View Scheme