1: 1.) mercuric bromide, cadmium carbonate, 2.) methanol / 1.) toluene, reflux, 24 h, 2.) H2O, 30 min 2: 1.) 2 M BCl3, 2.) CH3OH / 1.) CH2Cl2, -78 deg C, 5 h, 2.) CH2Cl2, from -78 deg C to RT, 1 h 3: 9 percent / 2-chloro-1,1,2-trifluorotriethylamine / dimethylformamide / 0.5 h / 70 °C 4: 42 percent / LiN3, NH4Cl / dimethylformamide / 18 h / 110 °C View Scheme

1: 1.) mercuric bromide, cadmium carbonate, 2.) methanol / 1.) toluene, reflux, 24 h, 2.) H2O, 30 min 2: 1.) 2 M BCl3, 2.) CH3OH / 1.) CH2Cl2, -78 deg C, 5 h, 2.) CH2Cl2, from -78 deg C to RT, 1 h View Scheme

1: 67 percent / acetic acid 2: 82 percent / CF3SO3SiMe3 / 1,2-dichloro-ethane / Ambient temperature 3: 40 percent / pyridine 4: 60 percent / BBr3 / CH2Cl2 View Scheme

<b>Multi-step reaction with 7 steps<br /> </b>1: aq. HCl / 0.5 h / Ambient temperature<br />2: NaH, Bu₄NI / tetrahydrofuran / 60 h / Ambient temperature<br />3: 85 percent / conc. HCl / 18 h / 40 &deg;C<br />4: 40 percent / PPh₃, diethyl azodicarboxylate / tetrahydrofuran / 18 h / Ambient temperature<br />5: 98 percent / NaOMe / CH₂Cl₂; methanol / 3 h / 0 - 20 &deg;C<br />6: 97 percent / pyridine / Ambient temperature<br />7: 38 percent / NaI, BaCO₃ / acetone / 42 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1: NaH, Bu₄NI / tetrahydrofuran / 60 h / Ambient temperature<br />2: 85 percent / conc. HCl / 18 h / 40 &deg;C<br />3: 40 percent / PPh₃, diethyl azodicarboxylate / tetrahydrofuran / 18 h / Ambient temperature<br />4: 98 percent / NaOMe / CH₂Cl₂; methanol / 3 h / 0 - 20 &deg;C<br />5: 97 percent / pyridine / Ambient temperature<br />6: 38 percent / NaI, BaCO₃ / acetone / 42 h / Heating<br /> <br /> &nbsp;