pyridinium chlorochromate in N,N-dimethyl-formamide T=20°C; 24 h;

Yield given. Multistep reaction;

oxalyl dichloride; dimethyl sulfoxide in dichloromethane 0.333333 h;

1.1: 91 percent / triethylamine / CH2Cl2 / -10 °C 2.1: 88 percent / lithium bromide / acetone / 72 h / 40 °C 3.1: 1,2-dibromoethane; magesium; iodine / zinc chloride / tetrahydrofuran / 2 h / 45 °C 3.2: 84 percent / (PPh3)4Pd / tetrahydrofuran / 24 h / 20 °C 4.1: 85 percent / tetra-n-butylammonium fluoride trihydrate / tetrahydrofuran / 4 h / 20 °C View Scheme

1.1: 91 percent / triethylamine / CH2Cl2 / -10 °C 2.1: 88 percent / lithium bromide / acetone / 72 h / 40 °C 3.1: 1,2-dibromoethane; magesium; iodine / zinc chloride / tetrahydrofuran / 2 h / 45 °C 3.2: 84 percent / (PPh3)4Pd / tetrahydrofuran / 24 h / 20 °C 4.1: 85 percent / tetra-n-butylammonium fluoride trihydrate / tetrahydrofuran / 4 h / 20 °C 5.1: 75 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / 0.5 h / -65 - 20 °C View Scheme

1.1: 91 percent / triethylamine / CH2Cl2 / -10 °C 2.1: 88 percent / lithium bromide / acetone / 72 h / 40 °C 3.1: 1,2-dibromoethane; magesium; iodine / zinc chloride / tetrahydrofuran / 2 h / 45 °C 3.2: 84 percent / (PPh3)4Pd / tetrahydrofuran / 24 h / 20 °C 4.1: 85 percent / tetra-n-butylammonium fluoride trihydrate / tetrahydrofuran / 4 h / 20 °C 5.1: 75 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / 0.5 h / -65 - 20 °C 6.1: magnesium; iodine; 1,2-dibromoethane / HgCl2 / tetrahydrofuran / 1 h / 5 - 15 °C 6.2: 76 percent / tetrahydrofuran / 1 h / 20 °C View Scheme

pyridine; phosphorus tribromide in diethyl ether 1.) RT, overnight, 2.) reflux, 2.5;

1H-imidazole; iodine; triphenylphosphine in tetrahydrofuran T=20°C;