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Potassium Carbonate → Methyl 4-(2-bromo-4,5-dimethoxybenzyloxy)-2-hydroxybenzoate

HRID 2167117
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2167117
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11].[Br:19][C:20]1[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[CH:24][C:21]=1[CH2:22]Br>CC(C)=O>[Br:19][C:20]1[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[CH:24][C:21]=1[CH2:22][O:18][C:16]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:8]([OH:7])[CH:17]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 16523Methyl 2,4-DihydroxybenzoateHCID 110342482-Bromo-4,5-dimethoxybenzyl bromide

Produkt 1

HCID 89464825Methyl 4-(2-bromo-4,5-dimethoxybenzyloxy)-2-hydroxybenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Potassium carbonate (1.12 g) was added to a solution of methyl 2,4-dihydroxybenzoate (454 mg) and 2-bromo-4,5-dimethoxybenzyl bromide (1.0 g) in dry acetone (80 ml). The reaction mixture was heated to reflux at 80° C. for 4 hours. The solvents were removed under vacuum and the residue was re-dissolved in DCM and washed with water (3×). The organic layer was passed through a hydrophobic frit and concentrated under vacuum. The crude residue was purified by chromatography on silica gel, eluting with petrol and increasing amounts of ethyl acetate.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. customThe solvents were removed under vacuum
  3. dissolutionthe residue was re-dissolved in DCM
  4. washwashed with water (3×)
  5. concentrationconcentrated under vacuum
  6. customThe crude residue was purified by chromatography on silica gel
  7. washeluting with petrol
  8. temperatureincreasing amounts of ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-8286cb9344cd46ddaac2e2ce705c6322
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09044463B2

Notizen zur Reaktion

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