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Potassium Carbonate → 5-Cyclopropyl-4-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxymethyl]-3-(2-trifluoromethoxy-phenyl)-isoxazole

HRID 250279
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 250279
Br[CH2:2][C:3]1[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][C:18]([F:21])([F:20])[F:19])=[N:5][O:6][C:7]=1[CH:8]1[CH2:10][CH2:9]1.[CH3:22][C:23]1[CH:24]=[C:25]([OH:38])[CH:26]=[CH:27][C:28]=1[B:29]1[O:33][C:32]([CH3:35])([CH3:34])[C:31]([CH3:37])([CH3:36])[O:30]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH:8]1([C:7]2[O:6][N:5]=[C:4]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][C:18]([F:21])([F:20])[F:19])[C:3]=2[CH2:2][O:38][C:25]2[CH:26]=[CH:27][C:28]([B:29]3[O:33][C:32]([CH3:34])([CH3:35])[C:31]([CH3:37])([CH3:36])[O:30]3)=[C:23]([CH3:22])[CH:24]=2)[CH2:10][CH2:9]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 574432723-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 669060924-(Bromomethyl)-5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]isoxazole

Produkt 1

HCID 672723615-Cyclopropyl-4-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxymethyl]-3-(2-trifluoromethoxy-phenyl)-isoxazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

To a 5-L 3-neck round bottom flask with a mechanical stirrer, thermocouple, reflux condenser, and drying tube is added 4-bromomethyl-5-cyclopropyl-3-(2-trifluoromethoxy-phenyl)-isoxazole (221.7 g, 0.612 mol, 1.05 eq), acetonitrile (2 L), 3-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (136.5 g, 0.583 mol, 1 eq) and potassium carbonate (241.8 g, 1.749 mol, 3 eq). The reaction mixture is heated to reflux and stirred at this temperature for 1 hour. Upon completion of the reaction, as evidenced by thin layer chromatography, the reaction mixture is cooled to 0-20° C. The reaction mixture is filtered and the filter cake is washed with acetonitrile (2×100 mL). The reaction mixture is concentrated under reduced pressure to a solid which is co-evaporated with 1,4-dioxane (500 mL). The title compound is used without further purification. 1H NMR (DMSO-d6, 300 MHz): δ 7.7-7.5 (m, 5H), 6.61 (m, 2H), 4.90 (s, 2H), 2.39 (m, 1H), 2.36 (s, 3H), 1.24 (s, 12H), 1.10 (m, 4H).

Aufarbeitung

  1. temperatureTo a 5-L 3-neck round bottom flask with a mechanical stirrer, thermocouple, reflux condenser
  2. customdrying tube
  3. temperatureThe reaction mixture is heated
  4. temperatureto reflux
  5. customUpon completion of the reaction
  6. filtrationThe reaction mixture is filtered
  7. washthe filter cake is washed with acetonitrile (2×100 mL)
  8. concentrationThe reaction mixture is concentrated under reduced pressure to a solid which
  9. customThe title compound is used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-ad958508a68b4fedb8d806a829f363ed
Quelldatensatz
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07863302B2

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