Potassium Carbonate → 2,5-Dichloro-4-(3-bromo-5-trifluoromethyl-2-pyridyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene

HRID 260776

Reaktionsgleichung

Reaktionsgleichung von HRID 260776
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:14]([Br:15])=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][N:10]=2)[C:5]([Cl:20])=[CH:4][C:3]=1[OH:21].C(=O)([O-])[O-].[K+].[K+].[Cl:28][C:29]([Cl:33])=[CH:30][CH2:31]Cl>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:14]([Br:15])=[CH:13][C:12]([C:16]([F:17])([F:19])[F:18])=[CH:11][N:10]=2)[C:5]([Cl:20])=[CH:4][C:3]=1[O:21][CH2:31][CH:30]=[C:29]([Cl:33])[Cl:28]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 173781,1,3-TrichloropropeneHCID 214663082,5-Dichloro-4-(3-bromo-5-trifluoromethyl-2-pyridyloxy)phenol

Produkt 1

HCID 214663982,5-Dichloro-4-(3-bromo-5-trifluoromethyl-2-pyridyloxy)-1-(3,3-dichloro-2-propenyloxy)benzeneAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a mixture of 0.77 g of 2,5-dichloro-4-(3-bromo-5-trifluoromethyl-2-pyridyloxy)phenol, 0.29 g of potassium carbonate and 20 ml of N,N-dimethylformamide, a solution prepared by dissolving 0.31 g of 1,1,3-trichloropropene in 5 ml of N,N-dimethylformamide was added dropwise at room temperature with stirring. After stirring at room temperature for 10 hours, the reaction solution was poured into ice-water, and extracted twice with 50 ml of ethyl acetate. Then, the ethyl acetate layers were combined, washed with water, dried over anhydrous magnesium sulfate and then concentrated to give a crude product. This crude product was subjected to silica gel chromatography to give 0.81 g of 2,5-dichloro-4-(3-bromo-5-trifiuoromethyl-2-pyridyloxy)-1-(3,3-dichloro-2-propenyloxy)benzene, yield 83%; m.p., 95.4° C.

Aufarbeitung

  1. customa solution prepared
  2. additionwas added dropwise at room temperature
  3. stirringAfter stirring at room temperature for 10 hours
  4. extractionextracted twice with 50 ml of ethyl acetate
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customto give a crude product

Quellen und Nachweise

ORD-Eintrag
ord-ef28b9322fc04263812c90391fac75d9
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05530015

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