Carbon tetrabromide → 4-(2,2-Dibromovinyl)-2-fluoro-1-methoxybenzene

HRID 1400606Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1400606
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=O.[C:12](Br)(Br)([Br:14])[Br:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:13][C:12]([Br:14])=[CH:5][C:4]1[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:2]([F:1])[CH:3]=1

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 676963-Fluoro-p-anisaldehyde

Produkt 1

HCID 594550774-(2,2-Dibromovinyl)-2-fluoro-1-methoxybenzeneAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-Fluoro-4-methoxy benzaldehyde (0.5 g, 0.00324 mol) was dissolved in DCM (30 mL). Carbon tetrabromide (2.15 g, 0.0064 mol) and triphenylphosphine (3.4 g, 0.013 mol) were added to the solution followed by stirring at RT for 3 h. Insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified through column chromatography (2% ethylacetate:hexane in silica 100-200 mesh) to provide the desired compound as a yellow colored oil (0.6 g, 60% yield).

Aufarbeitung

  1. customInsoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified through column chromatography (2% ethylacetate:hexane in silica 100-200 mesh)

Quellen und Nachweise

ORD-Eintrag
ord-5f0b8656fefb40e0939b107f79945d6f
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906925B2

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