1: 1.) n-BuLi, TMEDA, 2.) triisopropyl borate, 3.) tetrakis(triphenylphosphine)palladium, Na2CO3 2: 100 percent / Br2 / CCl4 / 0.67 h / 0 - 5 °C 3: 92 percent / aq. NaOH / methanol / 3 h / Heating 4: 18 percent / diphenylphosphorazidate, Et3N / dioxane / 20 h / Heating 5: 97 percent / NBS, benzoyl peroxide / CCl4 / 1.5 h / Heating; Irradiation 6: 62 percent / K2CO3 / dimethylformamide / 16 h / Ambient temperature 7: 98 percent / trifluoroacetic acid / CH2Cl2 / 16 h / Ambient temperature 8: 100 percent / Et3N / CH2Cl2 / 0.75 h / -70 °C 9: 95 percent / aq. NaOH / methanol / 3 h / 50 °C 10: 1.) CDI, 2.) NH3 / 1.) THF, RT, 3 h, 2.) THF, EtOH, a.) RT, 16 h, b.) reflux, 4 h View Scheme

N-bromosuccinmide; dibenzoyl peroxide in tetrachloromethane Bromination; 48 h; Heating;

N-bromosuccinmide in tetrachloromethane

N-bromosuccinmide in tetrachloromethane

poly-phosphoric acid in benzene 3.5 h; Heating;

sodium acetate; acetic anhydride T=110°C; 3 h;

hydrogenchloride in 2-methoxy-ethanol 4 h; Heating;

1: 1) sulphuryl chloride; 2) triethylamine / 1) CH2Cl2, -40 deg C, 20 min; 2) CH2Cl2, -40 to 20 deg C 2: potassium carbonate / methanol; H2O / 20 h / Ambient temperature 3: 45 percent / conc. HCl / 2-methoxy-ethanol / 4 h / Heating View Scheme

1: 81.6 percent / K2CO3 / tetrahydrofuran / 3 h / Heating 2: 83.3 percent / 20percent aq. KOH / ethanol / 0.5 h / 60 °C 3: 27.2 percent / AcONa, Ac2O / 3 h / 110 °C View Scheme

1: 90 percent / 4 h / 160 - 180 °C 2: 85 percent / aq. NaOH; tetrabutylammonium bromide / 4 h / Heating 3: 90 percent / KO-t-Bu / tetrahydrofuran / 0.5 h / Heating 4: 88 percent / Grubbs catalyst / CH2Cl2 / 8 h / 20 °C View Scheme