Ethyl 2-bromo-3-(4-methoxyphenyl)-3-oxopropanoate → HCID 59587379, Verbindung

HRID 389698Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 389698
Br[CH:2]([C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[F:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:20]=1[C:21]([O-:23])=[O:22].[Na+]>C(O)C.CCOC(C)=O.O>[F:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:20]=1[C:21]([O:23][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)=[O:9])=[O:22]

Komponenten

6

Edukt 2

HCID 13048360Ethyl 2-bromo-3-(4-methoxyphenyl)-3-oxopropanoateHCID 23698872Sodium 2,6-difluorobenzoate

Produkt 1

HCID 59587379HCID 59587379, VerbindungAusbeute 96,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of ethyl 2-bromo-3-(4-methoxyphenyl)-3-oxopropanoate (0.090 g, 0.3 mmol) and sodium 2,6-difluorobenzoate (0.054 g, 0.30 mmol) in ethanol (2 mL) was heated at 120° C. in the microwave for 10 minutes. The reaction mixture was diluted with EtOAc (25 mL) and water (25 mL). The organic phase was washed with water and brine, dried over MgSO4 and the solvent evaporated in vacuo. The residue was purified by silica gel column chromatography using a gradient of 0-40% EtOAc in hexanes to afford 3-ethoxy-1-(4-methoxyphenyl)-1,3-dioxopropan-2-yl 2,6-difluorobenzoate (0.108 g, 0.29 mmol, 96%) as a clear film. 1H NMR (CDCl3) δ 1.27 (3H, t), 3.89 (3H, s), 4.30 (2H, m), 6.47 (1H, s), 6.97 (4H, m), 7.46 (1H, m), 8.06 (2H, d). LCMS (1) Rt: 2.26 min; m/z (ES+) 379.

Aufarbeitung

  1. washThe organic phase was washed with water and brine
  2. dry with materialdried over MgSO4
  3. customthe solvent evaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-be4053e71b4a4939b2a17ea4c33a982b
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08378095B2

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