Sodium Iodide → 1-(4,4-Difluorobut-3-enyloxy)-3-((4-(difluoromethoxy)phenyl)ethynyl)benzene

HRID 30592

Reaktionsgleichung

[F:1][CH:2]([F:19])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=2)=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Br[CH2:29][CH2:30][CH:31]=[C:32]([F:34])[F:33]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C(C(C)=O)C.ClCCl>[F:33][C:32]([F:34])=[CH:31][CH2:30][CH2:29][O:18][C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([C:11]#[C:10][C:7]2[CH:6]=[CH:5][C:4]([O:3][CH:2]([F:19])[F:1])=[CH:9][CH:8]=2)[CH:13]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A mixture of 3-((4-(difluoromethoxy)phenyl)ethynyl)phenol (900 mg), potassium carbonate (636 mg), Aliquat 336 (4 drops), sodium iodide (catalytic) and 4-bromo-1,1-difluoro-1-butene (591 μL) in methyl ethyl ketone was placed in a pressure vessel, heated at 80° C. for 15 h, cooled to room temperature, diluted with dichloromethane and filtered. The filtrate was concentrated in vacuo. The resultant residue was purified by flash chromatography (silica gel, eluant: 2.5% ethyl acetate/hexane to afford 1-(4,4-difluorobut-3-enyloxy)-3-((4-(difluoromethoxy)phenyl)ethynyl)benzene, 560 mg (46.2% yield); 1H NMR (chloroform-d1): δ 7.51 (d, J=8.8 Hz, 2H), 7.24 (m, 1H), 7.10 (m, 1H), 7.08 (d, J=8.8 Hz, 2H), 7.03 (m, 1H), 6.87 (m, 1H), 6.52 (t, J=73.5 Hz, 1H), 4.32 (m, 1H), 3.97 (t, J=6.4 Hz, 2H) and 2.47 (m, J=6.4 Hz, 2H); MS (ES pos) m/z 350.

Aufarbeitung

customwas placed in a pressure vessel
temperaturecooled to room temperature
filtrationfiltered
concentrationThe filtrate was concentrated in vacuo
customThe resultant residue was purified by flash chromatography (silica gel, eluant

Quellen und Nachweise

ORD-Eintrag: ord-04f34b7d441e4224abcdfc90649b95ba
Quelldatensatz: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07423158B2

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