Triphenylphosphine → 3,5-Dichloro-4-(4-phenoxybenzyl)-1-(3,3-dichloro-2-propenyloxy)benzene

HRID 363060Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 363060
[Cl:1][C:2]([Cl:15])=[CH:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]([Cl:12])[C:9](O)=[C:8]([Cl:14])[CH:7]=1.[O:16]([C:23]1[CH:30]=[CH:29][C:26]([CH2:27]O)=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCCC1>[Cl:14][C:8]1[CH:7]=[C:6]([O:5][CH2:4][CH:3]=[C:2]([Cl:15])[Cl:1])[CH:11]=[C:10]([Cl:12])[C:9]=1[CH2:27][C:26]1[CH:29]=[CH:30][C:23]([O:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:24][CH:25]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 826195(4-Phenoxyphenyl)methanolHCID 5363146Diisopropyl azodicarboxylateHCID 113467384-(3,3-Dichloro-2-propenyloxy)-2,6-dichlorophenol

Produkt 1

HCID 538308253,5-Dichloro-4-(4-phenoxybenzyl)-1-(3,3-dichloro-2-propenyloxy)benzeneAusbeute 70,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 0.46 g of 4-(3,3-dichloro-2-propenyloxy)-2,6-dichlorophenol, 0.32 g of p-phenoxybenzyl alcohol and 0.46 g of triphenylphosphine dissolved in 10 ml of tetrahydrofuran was added dropwise a solution of 0.35 g of diisopropylazodicarboxylate dissolved in 5 ml of tetrahydrofuran, while stirring at room temperature. After stirring at room temperature for 12 hours, the reaction mixture was concentrated, and then mixed with 20 ml of diethyl ether. The precipitate was filtered, and the filtrate was concentrated. The residue was subjected to silica gel chromatography, which afforded 0.51 g of 3,5-dichloro-4-(4-phenoxybenzyl)-1-(3,3-dichloro-2-propenyloxy)benzene (68% yield), nD25.5 1.6084.

Aufarbeitung

  1. stirringAfter stirring at room temperature for 12 hours
  2. concentrationthe reaction mixture was concentrated
  3. additionmixed with 20 ml of diethyl ether
  4. filtrationThe precipitate was filtered
  5. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-a59277276c8a4d32953e1d9acc36a711
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05872137

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