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Phosphorus tribromide → 1-[4'-(4-Bromomethyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester

HRID 1512578
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1512578
P(Br)(Br)[Br:2].[CH2:5]([O:7][C:8]([C:10]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]4[O:29][N:28]=[C:27]([CH3:30])[C:26]=4[CH2:31]O)=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)[CH2:12][CH2:11]1)=[O:9])[CH3:6].C([O-])(O)=O.[Na+]>COCCOC>[CH2:5]([O:7][C:8]([C:10]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]4[O:29][N:28]=[C:27]([CH3:30])[C:26]=4[CH2:31][Br:2])=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)[CH2:12][CH2:11]1)=[O:9])[CH3:6]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 665772181-[4'-(4-Hydroxymethyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester

Produkt 1

HCID 665771991-[4'-(4-Bromomethyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8071
1,2-Dimethoxyethane
Lösungsmittel

Versuchsvorschrift

Phosphorus tribromide (0.43 mL, 4.53 mmol) was added to a solution of 1-[4′-(4-hydroxymethyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester (1.14 g, 3.02 mmol) in DME (30 mL) at 0° C. The reaction was stirred overnight at room temperature then cooled to 0° C. and neutralized with saturated aqueous NaHCO3 to pH 7. The mixture was partitioned between CH2Cl2 and H2O and the aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by silica gel chromatography to give the title compound.

Aufarbeitung

  1. customThe mixture was partitioned between CH2Cl2 and H2O
  2. extractionthe aqueous layer was extracted with CH2Cl2
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c0503a1b1e0a427794f73a556ab3e1c0
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08217066B2

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