1: 1.) n-BuLi / 1.) THFm HMPA, hexane, -80 deg C -> -30 deg C, 30 min; -30 deg C, 45 min, 2.) room temperature, 30 h 2: 87 percent / CBr4, Ph3P / CH2Cl2 / 0.75 h 3: 2.) CuCl / 1.) THF, room temperature, 2.5 h, 2.) 40 deg C, 3 h 4: 96 percent / Ni(OAc)4*4H2O, NaBH4, H2, ethylenediamine / aq. ethanol / 4 h 5: 69 percent / CBr4, Ph3P / CH2Cl2 / 0 °C 6: 380 mg / 12M HCl / methanol; tetrahydrofuran / 24 h / 0 °C View Scheme

1: 1.) n-BuLi / 1.) THFm HMPA, hexane, -80 deg C -> -30 deg C, 30 min; -30 deg C, 45 min, 2.) room temperature, 30 h 2: 87 percent / CBr4, Ph3P / CH2Cl2 / 0.75 h 3: 2.) CuCl / 1.) THF, room temperature, 2.5 h, 2.) 40 deg C, 3 h 4: 96 percent / Ni(OAc)4*4H2O, NaBH4, H2, ethylenediamine / aq. ethanol / 4 h 5: 69 percent / CBr4, Ph3P / CH2Cl2 / 0 °C 6: 142 mg / 12M HCl / methanol; tetrahydrofuran / 24 h / 0 °C View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '103853', constants.ctx, '0')">imidazole</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />T=0 - 20&deg;C;&nbsp;9&nbsp;h;&nbsp;<br /> &nbsp;