2-Fluorothiophenol → Ethyl 4-fluoro-alpha-[[(2-fluorophenyl)thio]methyl]benzeneacetate

HRID 22192

Reaktionsgleichung

Reaktionsgleichung von HRID 22192
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[CH2:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[SH:22].[O-]CC.[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:14][S:22][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[F:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 5202162-FluorothiophenolHCID 2723922Sodium ethoxideHCID 19736751HCID 19736751, Verbindung

Produkt 1

HCID 19927552Ethyl 4-fluoro-alpha-[[(2-fluorophenyl)thio]methyl]benzeneacetateAusbeute 82,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

The crude product from Step A (3.9 g, 20 mole) was taken up in 20 ml of ethanol. To this solution, being stirred at room temperature, was added 2-fluorothiophenol (2.5 g, 20 mmole) and 50 mg of solid sodium ethoxide. After stirring for eight hours the ethanol was concentrated and the residue taken up in ether. The ether mixture was washed twice with 15% NaOH solution, dried (MgSO4) and concentrated to a colorless oil (5.3 g, 82% yield). 1H NMR (CDCl3) δ: 7.28 (4H, m), 7.06 (4H, m), 4.13 (2H, m), 3.72 (1H, m), 3.55 (1H, m), 3.20 (1H, dd, J=6, 12 Hz), 1.21 (3H, t, J=6 Hz).

Aufarbeitung

  1. concentrationwas concentrated
  2. washThe ether mixture was washed twice with 15% NaOH solution
  3. dry with materialdried (MgSO4)

Quellen und Nachweise

ORD-Eintrag
ord-c5b877e7aced48708173e5628ebd3f82
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428027

Verknüpfte Notizen

Wird geladen…