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

HRID 1110676Notes

Reaction equation

HRID 1110676 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 1N 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 1N 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-0ef2489498094a65b6955a1421f5f37a
Source dataset
uspto-grants-1990_12
Patent number
US04976773

Reaction notes

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