Hydrogen Bromide → (6-Bromo-2-oxohexyl)(triphenyl)phosphanium bromide

HRID 1438830

Reaktionsgleichung

Reaktionsgleichung von HRID 1438830
[Br-:1].[O:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[CH:8][P+:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Br>>[Br-:1].[Br:1][CH2:7][CH2:6][CH2:5][CH2:4][C:3](=[O:2])[CH2:8][P+:9]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

3

Edukt 2

HCID 260Hydrogen BromideHCID 73676660[(tetrahydro-2H-pyran-2-ylidene)methyl]triphenylphosphonium bromide

Produkt 1

HCID 20369022(6-Bromo-2-oxohexyl)(triphenyl)phosphanium bromide

Versuchsvorschrift

A solution consisting of 1.6 parts of [(tetrahydro-2H-pyran-2-ylidene)methyl]triphenylphosphonium bromide in 25 parts by volume of 48% hydrobromic acid is heated at the reflux temperature for about 5 hours, then is stripped of solvent under reduced pressure to afford the crude product as an amber colored oil. Trituration of that oily material with benzene, followed by evaporation of the benzene under an atmosphere of nitrogen affords (6-bromo-2-oxohexyl)triphenylphosphonium bromide. This product exhibits 60-MHz nuclear magnetic resonance peaks in CDCl3 (deuterated chloroform) at about 100 cps (multiplet), 180 cps (multiplet), 200 cps (multiplet), 357 cps (doublet, J≃12 cps) in addition to the aromatic protons.

Aufarbeitung

  1. temperatureis heated at the reflux temperature for about 5 hours
  2. customto afford the crude product as an amber colored oil
  3. customTrituration of that oily material with benzene, followed by evaporation of the benzene under an atmosphere of nitrogen

Quellen und Nachweise

ORD-Eintrag
ord-107538741cc745ab881bada8e83b57a5
Quelldatensatz
uspto-grants-1977_11
Patentnummer
US04056562

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