3,4-Dichlorophenol → 2-(2-Nitro-4-trifluoromethylphenoxy)-4,5-dichlorobenzene

HRID 129872

Reaction equation

HRID 129872 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N+:21]([C:12]1[CH:13]=[C:14]([C:17]([F:18])([F:19])[F:20])[CH:15]=[CH:16][C:11]=1[O:9][C:4]1[CH:3]=[C:2]([Cl:1])[C:7]([Cl:8])=[CH:6][CH:5]=1)([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 72583,4-DichlorophenolHCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotolueneHCID 11430Potassium Carbonate

Product 1

HCID 13430092-(2-Nitro-4-trifluoromethylphenoxy)-4,5-dichlorobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3,4-dichlorophenol (25 gram (hereinafter g), 0.153 mol), 4-chloro-3-nitrobenzo-trifluoride (52 g, 0.23 mol) and potassium carbonate (63 g, 0.459 mol) in dimethylformamide (450 mL)was stirred under argon at 120° C. for 24 h. The reaction mixture was filtered and the filtrate evaporated. The residue was dissolved in ethyl acetate, washed with water, brine, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was flash chromatographed (silica gel, methylene chloride/hexane), to give the title compound as a yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate evaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customchromatographed (silica gel, methylene chloride/hexane)

Sources & evidence

ORD record
ord-2c6a3196267a4fda9525cf2daac82a75
Source dataset
uspto-grants-1995_11
Patent number
US05470882

Linked notes

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