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

HRID 1885512Notes

Reaction equation

HRID 1885512 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:6]([Cl:10])=[CH:5][C:3]=1N.[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18].N(OC(C)(C)C)=O>>[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:6]([Cl:10])=[CH:5][C:3]=1[C:16]1[CH:17]=[C:12]([Cl:11])[C:13]([Cl:18])=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 72391,2-DichlorobenzeneHCID 10906Tert-Butyl nitriteHCID 124872,4,5-Trichloroaniline

Product 1

HCID 358232,3',4,4',5-Pentachlorobiphenyl

Procedure

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.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux behind a safety shield for 90 min
  3. customThe excess 1,2-dichlorobenzene was removed in vacuo
  4. additionthe residue containing the product
  5. filtrationwas purified by filtration through silica gel following the method of E
  6. customCoward, Aldrichimica Acta, 1988, 21(4), 106-107, to give
  7. customafter crystallization from ethanol the title product (3 g, 9.3%)

Sources & evidence

ORD record
ord-363b54edfcb549d4b9abc3b36e2ea8eb
Source dataset
uspto-grants-1992_09
Patent number
US05145790

Reaction notes

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