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

HRID 515695
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 515695
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13].[Br-].[CH:17]1([CH2:23][Zn+])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>C1COCC1.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:17]1([CH2:23][C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=2[C:12]([F:15])([F:14])[F:13])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 14148738Methyl 4-chloro-3-(trifluoromethyl)benzoateHCID 178419774HCID 178419774, Verbindung

Produkt 1

HCID 67211598Methyl 4-(cyclohexylmethyl)-3-(trifluoromethyl)benzoateAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418851HCID 178418851, VerbindungKatalysatorHCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

To a stirred solution of methyl 4-chloro-3-(trifluoromethyl)benzoate (238 mg, 1.0 mmol) and bis(tri-t-butylphosphine)palladium (0) (51 mg, 0.10 mmol) in THF (2 mL) was added (cyclohexylmethyl)zinc(II) bromide (6 mL, 3.00 mmol) at room temperature. The reaction mixture was heated at reflux for 2 h, quenched with saturated NaHCO3 solution, and filtered through Celite®. The filtrate was extracted with ethyl acetate. The combined organics were dried and concentrated, and the residue was purified by silica gel column chromatography to give the title compound (280 mg) as a colorless oil. LCMS m/z=301.4. 1H NMR (400 MHz, CDCl3) δ ppm 0.96-1.06 (m, 2H), 1.14-1.22 (m, 3H), 1.62-1.72 (m, 6H), 2.71 (d, J=6.7 Hz, 2H), 3.94 (s, 3H), 7.39 (d, J=8.1 Hz, 1H), 8.10 (dd, J=8.0, 1.5 Hz, 1H), 8.30 (d, J=1.4 Hz, 1H).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. customquenched with saturated NaHCO3 solution
  4. filtrationfiltered through Celite®
  5. extractionThe filtrate was extracted with ethyl acetate
  6. customThe combined organics were dried
  7. concentrationconcentrated
  8. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2da0fb43eaa849ad88a53d22fcaa5c0d
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09108969B2

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