Water → 3,5-Dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(3,3-difluoro-2-propenyloxy)butyloxy)benzene

HRID 369658

Reaktionsgleichung

[Cl:1][C:2]1[CH:16]=[C:15]([O:17][CH2:18][CH:19]=[C:20]([Cl:22])[Cl:21])[CH:14]=[C:13]([Cl:23])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][CH2:10][CH:11]=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl[C:44]([F:49])([F:48])C([O-])=O.[Na+].O>COCCOCCOC>[Cl:1][C:2]1[CH:16]=[C:15]([O:17][CH2:18][CH:19]=[C:20]([Cl:22])[Cl:21])[CH:14]=[C:13]([Cl:23])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][CH2:10][CH:11]=[C:44]([F:49])[F:48]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

A mixture of 1.21 g of 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetaldehyde, 0.87 g of triphenylphosphine and 10 ml of diglyme was stirred at 160° C., to which a solution (5 ml) of 0.69 g of sodium chlorodifluoroacetate in diglyme heated to 60° C. was added dropwise. After stirring at 160° C. for 1.5 hours, the reaction mixture was returned to room temperature, poured into water and extracted twice with 50 ml of diethyl ether. The diethyl ether layers Were combined, washed with water, dried over magnesium sulfate and then concentrated to give a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.21 g of 3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-(4-(3,3-difluoro-2-propenyloxy)butyloxy)benzene (yield, 16%), nD23.0 1.5219.

Aufarbeitung

additionwas added dropwise
customwas returned to room temperature
extractionextracted twice with 50 ml of diethyl ether
washwashed with water
dry with materialdried over magnesium sulfate
concentrationconcentrated
customto give a crude product

Quellen und Nachweise

ORD-Eintrag: ord-a67d5650892d4378acaa41ca42f8aa1f
Quelldatensatz: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06140274

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