bromine; sodium acetate in acetic acid T=20 - 80°C;

bromine; sodium acetate in acetic acid 1.) 80 deg C, 6 h, 2.) 25 deg C, 16 h;

silver carbonate in benzene T=40 - 50°C; 24 h;

sodium methylate

bromine; sodium acetate in acetic acid 1.) 80 deg C, 6 h, 2.) 25 deg C, 16 h;;

sodium methylate T=50°C; 2 h; Cooling with ice;

1: 1.) n-BuLi / 1.) ether, hexane, -70 deg C, 15 min, 2.) ether, hexane, THF, -65 deg C 2: 83.5 percent / 48percent HBr, HOAc / 0.25 h / 100 °C 3: 59 percent / H2 / W-2 Raney Ni / tetrahydrofuran; ethanol / 6 h 4: 1.) t-BuLi / 1.) toluene, ether, pentane, -100 deg C, 20 min, 2.) toluene, ether, pentane, from -100 deg C to 0 deg C 5: 64 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 2 h / -25 - -5 °C View Scheme

trichlorophosphate in N,N-dimethyl-formamide T=105°C; 16 h;

1: 1.) n-BuLi / 1.) ether, hexane, -70 deg C, 15 min, 2.) ether, hexane, THF, -65 deg C 2: 83.5 percent / 48percent HBr, HOAc / 0.25 h / 100 °C 3: 59 percent / H2 / W-2 Raney Ni / tetrahydrofuran; ethanol / 6 h 4: 1.) t-BuLi / 1.) toluene, ether, pentane, -100 deg C, 20 min, 2.) toluene, ether, pentane, from -100 deg C to 0 deg C View Scheme

1: 1.) n-BuLi / 1.) ether, hexane, -70 deg C, 15 min, 2.) ether, hexane, THF, -65 deg C 2: 83.5 percent / 48percent HBr, HOAc / 0.25 h / 100 °C 3: 59 percent / H2 / W-2 Raney Ni / tetrahydrofuran; ethanol / 6 h 4: 1.) t-BuLi / 1.) toluene, ether, pentane, -100 deg C, 20 min, 2.) toluene, ether, pentane, - 95 deg C View Scheme