4-Chlorobenzaldehyde → 1-Chloro-4-(2,2-dibromoethenyl)benzene

HRID 1392772Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1392772
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10](Br)(Br)([Br:12])[Br:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:10]([Br:12])[Br:11])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 77264-ChlorobenzaldehydeHCID 11205Carbon tetrabromideHCID 11776Triphenylphosphine

Produkt 1

HCID 64229811-Chloro-4-(2,2-dibromoethenyl)benzeneAusbeute 93,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-Chlorobenzaldehyde (2.81 g) was dissolved in methylene chloride (300 ml), and carbon tetrabromide (13.3 g) and triphenylphosphine (21.0 g) were added to stir the mixture at room temperature for 90 minutes. After insoluble matter deposited was removed by filtration, the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=20:1) to obtain the title compound (5.54 g).

Aufarbeitung

  1. customAfter insoluble matter deposited was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-038ee91b26fd4cf682b70a022739b592
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342014B2

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