Dichloromethane → Benzoic acid, 2-chloro-5-cyclopropyl-, ethyl ester

HRID 41999

Reaktionsgleichung

Reaktionsgleichung von HRID 41999
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:13])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH:14]1(B2OC(C)(C)C(C)(C)O2)[CH2:16][CH2:15]1.C([O-])([O-])=O.[Cs+].[Cs+].C(Cl)Cl>O1CCOCC1.O>[Cl:13][C:5]1[CH:4]=[CH:3][C:2]([CH:14]2[CH2:16][CH2:15]2)=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 144749Ethyl 5-bromo-2-chlorobenzoateHCID 27580152-Cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Produkt 1

HCID 57422934Benzoic acid, 2-chloro-5-cyclopropyl-, ethyl esterAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

In a schlenck tube, a mixture of ethyl 5-bromo-2-chlorobenzoate (7.60 mmol, 2 g), 2-cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (7.59 mmol, 1.3 g), Cs2CO3 (18.97 mmol, 6.18 g), PdCl2dppf.CH2Cl2 (0.76 mmol, 0.620 g) in dioxane (70 ml) and water (15 ml) was heated for 2 hours at 110° C., under argon atmosphere. The solvent was evaporated and the mixture was extracted between ethyl acetate and water. The crude mixture was purified by chromatography over SiO2 eluting hexane/ethyl acetate mixtures and affording 1.5 g (yield 92%) of the expected product.

Aufarbeitung

  1. customThe solvent was evaporated
  2. extractionthe mixture was extracted between ethyl acetate and water
  3. customThe crude mixture was purified by chromatography over SiO2
  4. washeluting hexane/ethyl acetate mixtures

Quellen und Nachweise

ORD-Eintrag
ord-3f7a1f5c32b142a0a07a8e28ccfefc8f
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536165B2

Verknüpfte Notizen

Wird geladen…