(i) Et2O, (ii) HBr; Multistep reaction;

bromine various reactants ratio; Product distribution;

1: 78 percent / K2CO3, KI / acetone / 168 h / Ambient temperature 2: H2, acetic acid / 10percent Pd/C / methanol / 16 h / 2280 Torr 3: K2CO3 / acetone / 16 h / Ambient temperature 4: 1) KH, 2) HCl / 1) THF/hexane, 0 deg C, 2) MeOH, reflux, 2 h View Scheme

1: 95 percent / K2CO3, KI / acetone / 3 h 2: HCl / methanol / 1 h / Heating 3: NaCNBH3 / methanol / 1 h / Heating 4: K2CO3, KI / acetone / 16 h 5: 1) LDA, 2) HCl / 1) THF/hexane, -50 deg C, 30 min, 2) reflux, 4 h View Scheme

in N,N-dimethyl-formamide T=0 - 5°C; 0.5 - 0.583333 h;

1: With benzene Heating; 2: With sodium carbonate in water Further stages.;

1: benzene / Heating 2: Na2CO3 / H2O View Scheme

in ethyl acetate

1: 9.2 g / H2O / 4 h / Heating 2: 77 percent / BF3*OEt2 / CH2Cl2 / 4 h / Heating View Scheme

1.1: 95 percent / sodium formate dihydrate / ethanol / Heating 2.1: 92 percent / trifluoromethanesulfonic acid / cyclohexane; CH2Cl2 / 0 - 20 °C 3.1: 93 percent / potassium hydroxide / methanol; H2O / 20 °C 4.1: sodium hydroxide / toluene / Heating 5.1: methanol / 6 h / 0 °C 6.1: hydrogen chloride / methanol / 0 - 20 °C 6.2: p-toluenesulfonic acid / xylene / 200 - 210 °C 7.1: potassium hydroxide / methanol / 2 h / Heating 8.1: lithium; liquid ammonia / ethanol; tetrahydrofuran / 0.08 h / -40 °C 9.1: hydrochloric acid / H2O / Heating View Scheme