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

HRID 1885517Notes

Reaction equation

HRID 1885517 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

4

Reactant 2

HCID 124872,4,5-TrichloroanilineHCID 374383,4-Dichloroanisole

Product 2

HCID 198789142,4,4',5,5'-Pentachloro-2'-methoxy-1,1'-biphenylHCID 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.

Workup

  1. customThe excess dichloroanisole was removed by distillation
  2. filtrationthe residue was then filtered through silica gel (heptane eluent)
  3. customfurther purified [Chromatotron®, 4 mm silica gel, cyclohexane, 20 mL/min]

Sources & evidence

ORD record
ord-42bc2d9eaec54b2180731eb9dc9e82dc
Source dataset
uspto-grants-1992_09
Patent number
US05145790

Reaction notes

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