Methyl 4-chloro-3-(trifluoromethyl)benzoate → Methyl 4-cyclopentyl-3-(trifluoromethyl)benzoate

HRID 707756

Reaktionsgleichung

Reaktionsgleichung von HRID 707756
[CH:1]1([Mg]Cl)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[C:19]([F:22])([F:21])[F:20]>[Cl-].[Zn+2].[Cl-].CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH:1]1([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=2[C:19]([F:20])([F:22])[F:21])[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 2

HCID 14148738Methyl 4-chloro-3-(trifluoromethyl)benzoateHCID 178478989HCID 178478989, Verbindung

Produkt 1

HCID 11097668Methyl 4-cyclopentyl-3-(trifluoromethyl)benzoateAusbeute 95,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 178418851HCID 178418851, VerbindungKatalysator

Versuchsvorschrift

To zinc(II) chloride (0.5 M solution in tetrahydrofuran, 88.0 mL, 44.0 mmol) was added cyclopentylmagnesium chloride (2 M solution in ether, 20.5 mL, 41.1 mmol). The resulting suspension was stirred at room temperature for 1 h. To the above suspension was added methyl 4-chloro-3-(trifluoromethyl)benzoate (7.00 g, 29.3 mmol) and bis(tri-tert-butylphosphine)palladium (1.35 g, 2.64 mmol) at room temperature. The mixture was heated under reflux for 2 h. The mixture was allowed to cool to room temperature, quenched with saturated aqueous sodium bicarbonate solution and filtered. The filtrate was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure and purified by silica gel column chromatography to give the title compound as an oil (7.64 g). LCMS m/z=273.2 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.57-1.66 (m, 2H), 1.68-1.82 (m, 21H), 1.82-1.94 (m, 21H), 2.04-2.21 (m, 2H), 3.33-3.49 (m, 1H), 3.93 (s, 3H), 7.54 (d, J=8.21 Hz, 1H), 8.13 (dd, J=8.34, 1.77 Hz, 1H), 8.27 (s, 1H).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 h
  3. temperatureto cool to room temperature
  4. customquenched with saturated aqueous sodium bicarbonate solution
  5. filtrationfiltered
  6. extractionThe filtrate was extracted with ethyl acetate
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. custompurified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d097ac3d570440c38a066a54181dc19c
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09175320B2

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