Potassium Carbonate → 2-Bromo-4-(4-chlorophenylthio)-1-(3,3-dichloro-2-propenyloxy)benzene

HRID 260777

Reaktionsgleichung

Reaktionsgleichung von HRID 260777
[Br:1][C:2]1[CH:7]=[C:6]([S:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:16].C(=O)([O-])[O-].[K+].[K+].[Cl:23][C:24]([Cl:28])=[CH:25][CH2:26]Cl>CN(C)C=O>[Br:1][C:2]1[CH:7]=[C:6]([S:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:16][CH2:26][CH:25]=[C:24]([Cl:28])[Cl:23]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 173781,1,3-TrichloropropeneHCID 214663812-Bromo-4-(4-chlorophenylthio)phenol

Produkt 1

HCID 214662272-Bromo-4-(4-chlorophenylthio)-1-(3,3-dichloro-2-propenyloxy)benzeneAusbeute 78,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a mixture of 0.59 g of 2-bromo-4-(4-chlorophenylthio)phenol, 0.28 g of potassium carbonate and 20 ml of N,N-dimethylformamide, a solution prepared by dissolving 0.30 g of 1,1,3-trichloropropene in 5 ml of N,N-dimethylformamide was added dropwise at room temperature with stirring. After the mixture was stirred at room temperature for 6 hours, the reaction solution was poured into ice-water, and extracted twice with 50 ml of diethyl ether. Then, the ether 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 column chromatography to give 0.62 g of 2-bromo-4-(4-chlorophenylthio)-1-(3,3-dichloro-2-propenyloxy)benzene, yield 78%; nD25.0 1.6514.

Aufarbeitung

  1. customa solution prepared
  2. additionwas added dropwise at room temperature
  3. stirringAfter the mixture was stirred at room temperature for 6 hours
  4. extractionextracted twice with 50 ml of diethyl ether
  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-e268db84999b400a8fe36db33c5c8cfb
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05530015

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