1.1: sodium hydrogen carbonate; bromine / methanol; CCl4; H2O / 0.01 h / 20 °C 1.2: 63 percent / di-tert-butyl peroxyoxalate; diphenyl diselenide; tributyltin hydride / toluene / 2.5 h / 0 °C 2.1: 87 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / dimethylformamide / 1.33 h / 20 °C 3.1: hydrogen / Pd/C / tetrahydrofuran / 3 h / 20 °C 4.1: 6.5 mg / diethyl ether / 0.33 h / 20 °C View Scheme

1.1: sodium hydrogen carbonate; bromine / methanol; CCl4; H2O / 0.01 h / 20 °C 1.2: 63 percent / di-tert-butyl peroxyoxalate; diphenyl diselenide; tributyltin hydride / toluene / 2.5 h / 0 °C 2.1: 87 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / dimethylformamide / 1.33 h / 20 °C View Scheme