Sodium Iodide → (S)-2,4-difluoro-1-(2-iodomethyl-butyl)-benzene

HRID 132646Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 132646
[F:1][C:2]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:3]=1[CH2:4][C@H:5]([CH2:12][CH3:13])[CH2:6]OS(C)(=O)=O.[I-:19].[Na+]>CC(C)=O>[F:1][C:2]1[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:3]=1[CH2:4][C@@H:5]([CH2:6][I:19])[CH2:12][CH3:13]

Komponenten

4

Edukt 2

HCID 5238Sodium IodideHCID 87760874(2S)-methanesulfonic acid 2-(2,4-difluoro-benzyl)-butyl ester

Produkt 1

HCID 69268259(S)-2,4-difluoro-1-(2-iodomethyl-butyl)-benzeneAusbeute 91,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A flask was charge with 9.54 g (34.3 mmol) of (2S)-methanesulfonic acid 2-(2,4-difluoro-benzyl)-butyl ester, 10.3 g (68.6 mmol) of sodium iodide, and 60 mL of acetone. The solution was heated at reflux for 30 hours. The acetone was removed under reduced pressure. The residue was partitioned between water and hexanes. The organic layer was collected and washed with sodium bisulfite solution and brine. The hexane was removed under reduced pressure, and the crude oil was purified by column chromatography (hexanes eluent). This procedure gave 9.7 g (91% yield) of the titled compound as a clear oil.

Aufarbeitung

  1. temperatureThe solution was heated
  2. temperatureat reflux for 30 hours
  3. customThe acetone was removed under reduced pressure
  4. customThe residue was partitioned between water and hexanes
  5. customThe organic layer was collected
  6. washwashed with sodium bisulfite solution and brine
  7. customThe hexane was removed under reduced pressure
  8. customthe crude oil was purified by column chromatography (hexanes eluent)

Quellen und Nachweise

ORD-Eintrag
ord-d421ab7bbf0a47adaa95bb9fca454bbf
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07388023B2

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