Water → 4-Chloro-2-(3-chloromethyl-2-methysulfanyl-phenoxy)-benzonitrile

HRID 1178541

Reaktionsgleichung

[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17]N(C)C)[C:12]=2[S:21][CH3:22])[CH:3]=1.[Cl:23]C(OCC)=O.O.C(OCC)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][Cl:23])[C:12]=2[S:21][CH3:22])[CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Under a nitrogen atmosphere, 4-chloro-2-(3-dimethylaminomethyl-2-methysulfanyl-phenoxy)-benzonitrile (1.02 g, 3.06 mmol) was dissolved in anhydrous toluene (10 mL). The solution was cooled to 0° C. and ethyl chloroformate (900 μL, 9.2 mmol) was slowly added. The reaction mixture was stirred for 17 h, allowing it to reach room temperature. Water (5 mL) and diethyl ether (5 mL) were added and the organic layer was separated and dried with MgSO4. After filtration, the solution was absorbed onto silica gel (1.5 g) and the solvent was removed in vacuo. This material was chromatographed on an ISCO CombiFlash Chromatography System to yield 4-chloro-2-(3-chloromethyl-2-methysulfanyl-phenoxy)-benzonitrile as a clear oil (800 mg, 81%).

Aufarbeitung

customto reach room temperature
customthe organic layer was separated
dry with materialdried with MgSO4
filtrationAfter filtration
customthe solution was absorbed onto silica gel (1.5 g)
customthe solvent was removed in vacuo
customThis material was chromatographed on an ISCO CombiFlash Chromatography System

Quellen und Nachweise

ORD-Eintrag: ord-10169752880f440f8f18abb1dbae1fd8
Quelldatensatz: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07276528B2

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