2,3-Dinitrophenol → Ethyl 2-(2,3-dinitrophenoxy)acetate

HRID 415096

Reaktionsgleichung

Reaktionsgleichung von HRID 415096
[N+:1]([C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[OH:13])([O-:3])=[O:2].Br[CH2:15][C:16]([O:18][C:19](C)(C)[CH3:20])=[O:17].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[N+:1]([C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[O:13][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 61912,3-DinitrophenolHCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetate

Produkt 1

HCID 86642030Ethyl 2-(2,3-dinitrophenoxy)acetateAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A round-bottom flask was charged with 2,3-dinitrophenol (11.04 g, 60 mmol, commercially available from Fluka-Sigma-Aldrich), tert-butyl bromoacetate (14.05 g, 66 mmol), acetonitrile (120 mL) and cesium carbonate (21.6 g). The mixture was stirred at room temperature overnight. The mixture was filtered, and the recovered solid was washed with ethyl acetate. The filtrate was further diluted with ethyl acetate and water. The aqueous layer was extracted with ethyl acetate and combined organic solvent was washed with saturated brine, dried and concentrated under reduced pressure. The residue was triturated with ether to give ethyl 2-(2,3-dinitrophenoxy)acetate (13.0 g, 70% yield). 1H-NMR (DMSO-d6) δ 7.84 (d, 2H), 7.42 (s, 1H), 4.90 (s, 2H), 1.40 (S, 9H).

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. washthe recovered solid was washed with ethyl acetate
  3. additionThe filtrate was further diluted with ethyl acetate and water
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washwas washed with saturated brine
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was triturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-b12faa9f3aab45d38b7a14f8b7d45680
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08088767B2

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