2,4,5-Trichloroaniline → 2,4,4',5,5'-Pentachloro-2'-methoxy-1,1'-biphenyl

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([O:9][CH3:10])[CH:5]=[CH:6][C:7]=1[Cl:8].[Cl:11][C:12]1[CH:18]=[C:17]([Cl:19])[C:16]([Cl:20])=[CH:15][C:13]=1N>>[CH3:10][O:9][C:4]1[CH:3]=[C:2]([Cl:1])[C:7]([Cl:8])=[CH:6][C:5]=1[C:13]1[CH:15]=[C:16]([Cl:20])[C:17]([Cl:19])=[CH:18][C:12]=1[Cl:11].[CH3:10][O:9][C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[C:3]=1[C:13]1[CH:15]=[C:16]([Cl:20])[C:17]([Cl:19])=[CH:18][C:12]=1[Cl:11]

Participants

Reactant 2

HCID 124872,4,5-Trichloroaniline

HCID 374381,2-Dichloro-4-methoxybenzene

Product 2

HCID 198789142,4,4',5,5'-Pentachloro-2'-methoxy-1,1'-biphenyl

HCID 19878939HCID 19878939, compound

Procedure

2-Methoxy-2',4,4',5,5'-pentachlorobiphenyl was prepared from 3,4-Dichloroanisole (35 g, 200 mmol) and 2,4,5-trichloroaniline (2.95 g, 15 mmol) according to the procedure in Example 2A. The excess dichloroanisole was removed by distillation and the residue was then filtered through silica gel (heptane eluent) and further purified [Chromatotron®, 4 mm silica gel, cyclohexane, 20 mL/min] to give 2-methoxy-2',4,4',5,5'-pentachlorobiphenyl (700 mg) and 2-Methoxy-2',4',5,5',6-pentachlorobiphenyl (1.2 g). Mass spectrum: m/z at 354 for C13H7Cl5O.