Methyl Ethyl Ketone → Ethyl (5-bromobenzofuran)-2-carboxylate

HRID 902017

Reaktionsgleichung

Reaktionsgleichung von HRID 902017
[Br:1][C:2]1[CH:9]=[C:6]([CH:7]=O)[C:5]([OH:10])=[CH:4][CH:3]=1.C([C:13](CC)([C:18]([O-:20])=[O:19])C(OBr)=O)C.C(=O)([O-])[O-].[K+].[K+].[CH2:29](C(C)=O)[CH3:30]>>[CH2:29]([O:20][C:18]([C:13]1[O:10][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:9][C:6]=2[CH:7]=1)=[O:19])[CH3:30]

Komponenten

5

Edukt 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 728635-BromosalicylaldehydeHCID 86590788Bromo diethylmalonate

Produkt 1

HCID 735184Ethyl (5-bromobenzofuran)-2-carboxylateAusbeute 78 %

Versuchsvorschrift

A solution of 5-bromo-salicylaldehyde (5.0 g, 25 mmol) and bromo diethylmalonate (8.9 g, 37 mmol) in methyl ethyl ketone (50 mL) is treated with potassium carbonate (6.8 g, 50 mmol) and heated to reflux. The reaction is stirred over 3 days at reflux. The reaction is then concentrated to a crude solid that is purified by silica gel column chromatography (9:1 hexane/EtOAc) to afford 5.2 g (78%) of the desired product. 1H NMR (CDCl3) 7.81 (d, 1H), 7.26-7.55 (m, 3H), 4.44 (q, 2H), 1.42 (t, 3H).

Aufarbeitung

  1. temperatureheated to reflux
  2. temperatureat reflux
  3. concentrationThe reaction is then concentrated to a crude solid
  4. customthat is purified by silica gel column chromatography (9:1 hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-dcd1e3fcb5a746e995bd0fae885d2464
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07365066B2

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