Potassium Carbonate → 4-(4-Bromo-3-methyl-phenoxymethyl)-5-cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazole

HRID 250295

Reaktionsgleichung

Reaktionsgleichung von HRID 250295
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].Br[CH2:11][C:12]1[C:13]([C:20]2[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:27])=[N:14][O:15][C:16]=1[CH:17]1[CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:11][C:12]2[C:13]([C:20]3[C:21]([Cl:27])=[CH:22][CH:23]=[CH:24][C:25]=3[Cl:26])=[N:14][O:15][C:16]=2[CH:17]2[CH2:19][CH2:18]2)=[CH:4][C:3]=1[CH3:9]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 728574-Bromo-m-cresolHCID 593693284-(Bromomethyl)-5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazole

Produkt 1

HCID 672715854-(4-Bromo-3-methyl-phenoxymethyl)-5-cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazoleAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of 4-bromo-3-methyl-phenol (143 mg, 0.764 mmol) and 4-bromomethyl-5-cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazole (221 mg, 0.636 mmol) in dimethylformamide (1 mL) is treated with potassium carbonate (89 mg, 0.637-mmol). The reaction mixture is heated to 80° C. for 60 minutes and cooled to room temperature. The mixture is loaded directly onto a silica gel column and purified by flash chromatography eluting with 15% EtOAc/Hexanes. The fractions are combined to provide the title compound (0.26 g, 92%). LC-MS: (M+1);

Aufarbeitung

  1. temperaturecooled to room temperature
  2. custompurified by flash chromatography
  3. washeluting with 15% EtOAc/Hexanes

Quellen und Nachweise

ORD-Eintrag
ord-b4b2d7ecc9704eb299c1c32af5245325
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863302B2

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