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

HRID 1885516Notes

Reaction equation

HRID 1885516 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[O:9][CH3:10].[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:3]1[C:2]([Cl:1])=[CH:7][C:6]([C:13]2[CH:15]=[C:16]([Cl:20])[C:17]([Cl:19])=[CH:18][C:12]=2[Cl:11])=[C:5]([Cl:8])[CH:4]=1

Participants

3

Reactant 2

HCID 124872,4,5-TrichloroanilineHCID 161252,5-Dichloroanisole

Product 1

HCID 220135312,2',4,5,5'-Pentachloro-4'-methoxy-1,1'-biphenyl

Procedure

4-Methoxy-2,2',4',5,5'-pentachlorobiphenyl was prepared from 2,5-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, hexane, 20 mL/min] to give the product (980 mg). 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, hexane, 20 mL/min]

Sources & evidence

ORD record
ord-f96888fa5e4648ea8bb5cebdc3c08805
Source dataset
uspto-grants-1992_09
Patent number
US05145790

Reaction notes

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