1,2-Dichlorobenzene → 2,3',4,4',5-Pentachlorobiphenyl

Participants

Reaction Steps

2',4,4',5,5'-pentachlorobiphenyl was prepared according to the standard procedure of Cadogan [J. I. G. Cadogan, J. Chem. Soc. (London), 1962, 4257-58]. Thus, 2,4,5-trichloroaniline (20 g, 0.1 mol) was dissolved in 1,2-dichlorobenzene (125 mL, 1.1 mol). t-Butyl nitrite (28.2 mL, 1.1 mol) was introduce to the stirred solution in three portions over 10 min. After 15 min the evolution of gas had subsided, and the reaction mixture was heated to reflux behind a safety shield for 90 min, and then stirred at ambient temperature for 12 h. The excess 1,2-dichlorobenzene was removed in vacuo and the residue containing the product was purified by filtration through silica gel following the method of E. K. Yau and J. K. Coward, Aldrichimica Acta, 1988, 21(4), 106-107, to give after crystallization from ethanol the title product (3 g, 9.3%). Mass spectrum: m/z at 324 for C12H5Cl5.

Provenance & Evidence