Sodium hydride → 1-(4-Bromo-2-nitro-phenoxy)-cyclopropanecarboxylic acid ethyl ester

HRID 2209277

Reaktionsgleichung

Reaktionsgleichung von HRID 2209277
[H-].[Na+].[OH:3][C:4]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH2:5]1.[Br:12][C:13]1[CH:18]=[CH:17][C:16](F)=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=1>C1COCC1.C1OCCOCCOCCOCCOC1.C(OCC)(=O)C>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([O:3][C:4]2([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH2:5]2)=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=1

Komponenten

7

Edukt 3

HCID 24758Sodium hydrideHCID 2733706Ethyl 1-hydroxycyclopropane-1-carboxylateHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Produkt 1

HCID 583407841-(4-Bromo-2-nitro-phenoxy)-cyclopropanecarboxylic acid ethyl esterAusbeute 66,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3633615-Crown-5KatalysatorHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Sodium hydride (60%, 166 mg, 4.15 mmol) was added to a solution of ethyl 1-hydroxycyclopropanecarboxylate (0.41 mL, 3.59 mmol) in THF (10 mL) at room temperature. After 15 min, 3 drops of 15-crown-5 were added followed by 4-bromo-1-fluoro-2-nitrobenzene (0.42 mL, 3.41 mmol). Mixture was stirred at room temperature for 24 hours. After diluting with 50 mL of ethyl acetate, mixture was quenched by addition of brine (25 mL) and layers were separated. Aqueous phase was extracted with ethyl acetate and combined organics were dried (MgSO4), filtered, and concentrated under reduced pressure. Resulting residue was purified via silica gel column chromatography (0-30% ethyl acetate/hexanes) to yield ethyl 1-(4-bromo-2-nitrophenoxy)cyclopropanecarboxylate 7.20 (750 mg)

Aufarbeitung

  1. customwas quenched by addition of brine (25 mL) and layers
  2. customwere separated
  3. extractionAqueous phase was extracted with ethyl acetate
  4. dry with materialcombined organics were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customResulting residue was purified via silica gel column chromatography (0-30% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-faca75f7960544ebb89e4f0a3c66e48f
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09376441B2

Verknüpfte Notizen

Wird geladen…