Triethylamine → 2-(4-(3-Chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy)propionic acid 5-(2,4-dichlorophenoxy)-2-nitrophenyl ester

HRID 1591018Notes

Reaction equation

HRID 1591018 reaction equation
[Cl:1][C:2]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[C:9]([OH:11])[CH:10]=1.C(N(CC)CC)C.[Cl:27][C:28]1[C:29]([O:38][C:39]2[CH:50]=[CH:49][C:42]([O:43][CH:44]([CH3:48])[C:45](Cl)=[O:46])=[CH:41][CH:40]=2)=[N:30][CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1>O1CCCC1>[Cl:1][C:2]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:12]([O-:14])=[O:13])=[C:9]([O:11][C:45](=[O:46])[CH:44]([O:43][C:42]2[CH:41]=[CH:40][C:39]([O:38][C:29]3[C:28]([Cl:27])=[CH:33][C:32]([C:34]([F:35])([F:36])[F:37])=[CH:31][N:30]=3)=[CH:50][CH:49]=2)[CH3:48])[CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1812285-(2,4-Dichlorophenoxy)-2-nitrophenolHCID 13389070HCID 13389070, compound

Product 1

HCID 147217182-(4-(3-Chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy)propionic acid 5-(2,4-dichlorophenoxy)-2-nitrophenyl esterYield 66.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5-(2,4-Dichlorophenoxy)-2-nitrophenol (0.8 g) and triethylamine (0.6 ml) were dissolved in dry tetrahydrofuran (10 ml), and the solution was stirred at room temperature for 2 hours, with an addition of a solution of 2-(4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy)propionic acid chloride (0.8 g), in dry tetrahydrofuran (10 ml). After completing the reaction, the solvent was distilled off under a reduced pressure and the residue was dissolved in methylene chloride (20 ml), followed by washing with 1 N hydrochloric acid, water, a saturated aqueous sodium bicarbonate solution, water, and a saturated aqueous sodium chloride solution. The resultant reaction mixture was dried over anhydrous magnesium sulfate, ether was evaporated under a reduced pressure, and the resultant residue was subjected to silica gel medium pressure column chromatography for purification. Thus, the title compound (0.9 g) was obtained in the form of a colorless oily product.

Workup

  1. customthe reaction
  2. distillationthe solvent was distilled off under a reduced pressure
  3. dissolutionthe residue was dissolved in methylene chloride (20 ml)
  4. washby washing with 1 N hydrochloric acid, water
  5. customThe resultant reaction mixture
  6. dry with materialwas dried over anhydrous magnesium sulfate, ether
  7. customwas evaporated under a reduced pressure
  8. customthe resultant residue was subjected to silica gel medium pressure column chromatography for purification

Sources & evidence

ORD record
ord-11e6089e911d4100a571be541956e6b0
Source dataset
uspto-grants-1993_04
Patent number
US05205855

Reaction notes

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