2,6-Dichlorobenzoic acid → 2,6-Dichlorobenzoyloxymethyl ketone

HRID 225946

Reaktionsgleichung

Reaktionsgleichung von HRID 225946
Br[CH2:2][C:3]([CH2:5]Br)=[O:4].[Cl:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:9]=1[C:10]([OH:12])=[O:11].[F-].[K+]>CN(C)C=O>[Cl:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:9]=1[C:10]([O:12][CH2:2][C:3]([CH2:5][O:12][C:10](=[O:11])[C:9]1[C:8]([Cl:7])=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:17])=[O:4])=[O:11]

Komponenten

5

Edukt 3

HCID 57582,6-Dichlorobenzoic acidHCID 699521,3-Dibromo-2-propanoneHCID 522689Potassium Fluoride

Produkt 1

HCID 185175242,6-Dichlorobenzoyloxymethyl ketone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Thus obtained bromomethyl ketone derivative (X, 4.36 g) and 2,6-dichlorobenzoic acid (2.28 g, 1.1 Eq) were dissolved in dimethylformamide (18 ml), KF (1.58 g, 2.5 Eq) was added, and the mixture was stirred for two hours to give 2,6-dichlorobenzoyloxymethyl ketone derivative (XIa). This compound was dissolved in methanol (20 ml) and reacted by adding NaBH4 (412 mg)-methanol solution (40 ml)(−10□˜room temperature, two hours). The reaction was stopped by acetic acid, and the reaction solution was distilled under reduced pressure to remove methanol. The residue was extracted with ethyl acetate (50 ml×2), washed with water and aqueous sodium chloride solution, dried (anhydrous Na2SO4), concentrated under reduced pressure, and separated-purified by column chromatography (ethyl acetate-hexane, 1:5) to give the title compound (4.80 g, Yield 86%) in a diastereomeric form.

Quellen und Nachweise

ORD-Eintrag
ord-f12c119bc359443caf7f777dfcfb8f5d
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557133B2

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