Tetrahydrofuran → 3-Chloro-2-(trifluoromethyl)phenylacetonitrile

HRID 1749489Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1749489
CS(O[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:8]=1[C:14]([F:17])([F:16])[F:15])(=O)=O.C[Si](C)(C)[C:20]#[N:21].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>C(#N)C.O.C(OCC)(=O)C>[Cl:13][C:9]1[C:8]([C:14]([F:17])([F:16])[F:15])=[C:7]([CH2:6][C:20]#[N:21])[CH:12]=[CH:11][CH:10]=1

Komponenten

8

Edukt 4

HCID 8028TetrahydrofuranHCID 82115Trimethylsilyl cyanideHCID 2724141Tetrabutylammonium FluorideHCID 1181621493-Chloro-2-(trifluoromethyl)benzyl methanesulfonate

Produkt 1

HCID 1181621683-Chloro-2-(trifluoromethyl)phenylacetonitrileAusbeute 583,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 3-chloro-2-(trifluoromethyl)benzyl methanesulfonate (0.150 g, crude) and trimethylsilanecarbonitrile (119 mg, 1.2 mmol) in acetonitrile (5 mL) was added a solution of tetrabutylammonium fluoride in THF (1M, 1.2 mL, 1.2 mmol). The reaction was stirred at room temperature for 2 h. The reaction was treated with ethyl acetate and water, and the separated organic layer was washed with brine, dried and concentrated to give the crude product, which was purified by silica gel column chromatography (10% ethyl acetate in petroleum ether) to afford the title compound (0.10 g, 3.03 mmol, 68% yield over three steps) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ (ppm) 7.56-7.48 (m, 3H), 3.99 (d, J=2.0 Hz, 2H).

Aufarbeitung

  1. washthe separated organic layer was washed with brine
  2. customdried
  3. concentrationconcentrated
  4. customto give the crude product, which
  5. customwas purified by silica gel column chromatography (10% ethyl acetate in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-0c9564ea0347453c81c33ceba4509fde
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156798B2

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