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Potassium Carbonate → 3-(4-Bromo-2-formyl-phenoxy)-2,2-dimethyl-propionic acid methyl ester

HRID 1728178
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1728178
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH3:11][O:12][C:13](=[O:29])[C:14]([CH3:28])([CH3:27])[CH2:15]OS(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:11][O:12][C:13](=[O:29])[C:14]([CH3:28])([CH3:27])[CH2:15][O:10][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:9][C:6]=1[CH:7]=[O:8]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 728635-BromosalicylaldehydeHCID 22479327Methyl 3-(p-tolylsulfonyloxy)-2,2-dimethylpropanoate

Produkt 1

HCID 575659193-(4-Bromo-2-formyl-phenoxy)-2,2-dimethyl-propionic acid methyl esterAusbeute 904,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228Dimethylformamide
Lösungsmittel

Versuchsvorschrift

5-Bromo-2-hydroxy-benzaldehyde (4 g, 2 mmol), 2,2-dimethyl-3-(toluene-4-sulfonyloxy)-propionic acid methyl ester (5.46 g, 24 mmol), K2CO3 (5.5 g, 40 mmol) and KI (0.1 g) were mixed in DMF (20 mL). Then the mixture was irradiated under microwave at 150° C. for 1 h. The mixture was filtered and the filtrate was concentrated. The residue was dissolved in ethyl acetate and washed with 1N NaOH. Then the organic layer was separated, dried over Na2SO4 and concentrated to give title compound 5.7 g.

Aufarbeitung

  1. customThen the mixture was irradiated under microwave at 150° C. for 1 h
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with 1N NaOH
  6. customThen the organic layer was separated
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-433e15e370e94c9392ad3d4f37f5b16b
Quelldatensatz
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07495007B2

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