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

HRID 616780

Reaktionsgleichung

Reaktionsgleichung von HRID 616780
[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 was heated at the reflux temperature for about 5 hours, then was stripped of solvent under reduced pressure affording 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 afforded (6-bromo-2-oxohexyl)triphenylphosphonium bromide. This product exhibited 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. temperaturewas heated at the reflux temperature for about 5 hours
  2. customaffording 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-92985b6c0829403ba1895ccfb2e8db51
Quelldatensatz
uspto-grants-1978_02
Patentnummer
US04075407

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