Sodium hydride → rac-Ethyl 2-(3-bromo-4-fluorophenyl)-trans-cyclopropanecarboxylate

HRID 1476066Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1476066
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[Br:9][C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:13]=[CH:14][C:15]=1[F:16]>CS(C)=O>[Br:9][C:10]1[CH:11]=[C:12]([C@@H:17]2[CH2:4][C@H:18]2[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:13]=[CH:14][C:15]=1[F:16]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 67207802Ethyl 3-(3-bromo-4-fluorophenyl)acrylate

Produkt 1

HCID 123400670rac-Ethyl 2-(3-bromo-4-fluorophenyl)-trans-cyclopropanecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Under argon, 381 mg (9.52 mmol) of sodium hydride (60% in paraffin oil) were initially charged in 20 ml of DMSO, and 2.1 g (9.52 mmol) of trimethylsulphoxonium iodide were added in one portion at RT. After the evolution of gas had ceased, 2.0 g (7.3 mmol) of ethyl 3-(3-bromo-4-fluorophenyl)acrylate, dissolved in 10 ml of DMSO, were slowly added dropwise. The reaction mixture was heated at 50° C. overnight, then cooled to RT and, without further work-up, purified by flash chromatography on silica gel (mobile phase isohexane/ethyl acetate 100:1). This gave 907 mg (43% of theory) of the target product.

Aufarbeitung

  1. additionwere slowly added dropwise
  2. temperaturecooled to RT and, without further work-up
  3. custompurified by flash chromatography on silica gel (mobile phase isohexane/ethyl acetate 100:1)

Quellen und Nachweise

ORD-Eintrag
ord-5f2a185aa369410ca150ee31180e1454
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09018414B2

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