Tetrabutylammonium Fluoride → 4-Chloro-1-ethynyl-2-fluorobenzene

HRID 59333

Reaktionsgleichung

Reaktionsgleichung von HRID 59333
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][Si](C)(C)C)=[C:4]([F:14])[CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[C:4]([F:14])[CH:3]=1

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 90019293((4-Chloro-2-fluorophenyl)ethynyl)trimethylsilane

Produkt 1

HCID 509987944-Chloro-1-ethynyl-2-fluorobenzeneAusbeute 73,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of ((4-chloro-2-fluorophenyl)ethynyl)trimethylsilane (1.0 g, 4.42 mmol) in DCM (20 mL) was added TBAF (catalytic) and reaction mixture was stirred for 1-2 h at RT. The reaction mass was quenched in water, extracted with DCM and concentrated to afford 0.900 g of the crude product which was further purified by column chromatography eluting with pet. ether to afford to afford 0.500 g of pure product. 1H NMR (300 MHz, DMSO d6): δ 4.60 (s, 1H), 7.32 (d, J=8.1 Hz, 1H), 7.56-7.61 (m, 2H).

Aufarbeitung

  1. customThe reaction mass was quenched in water
  2. extractionextracted with DCM
  3. concentrationconcentrated
  4. customto afford 0.900 g of the crude product which
  5. customwas further purified by column chromatography
  6. washeluting with pet. ether
  7. customto afford

Quellen und Nachweise

ORD-Eintrag
ord-c89a7419ef5c4f178e8a5c1eb06a8e57
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09439890B2

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