Potassium Carbonate → 3-(2-Methoxyphenyl)-4,5-methylenedioxybenzaldehyde

HRID 860533

Reaktionsgleichung

Reaktionsgleichung von HRID 860533
Br[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]2[O:12][CH2:11][O:10][C:9]=12)[CH:5]=[O:6].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]2[O:12][CH2:11][O:10][C:9]=12)[CH:5]=[O:6]

Komponenten

8

Edukt 3

HCID 11430Potassium CarbonateHCID 23202437-Bromo-1,3-dioxaindane-5-carbaldehydeHCID 27339582-Methoxyphenylboronic acid

Produkt 1

HCID 865860323-(2-Methoxyphenyl)-4,5-methylenedioxybenzaldehydeAusbeute 32,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 3-bromo-4,5-methylenedioxybenzaldehyde (2.51 g, 10.97 mmol), 2-methoxyphenylboronic acid (2.00 g, 13.16 mmol) and potassium carbonate (3.41 g, 24.68 mmol) in 1,2-dimethoxyethane (70 mL) and water (3.5 mL) was degassed with argon for 30 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.63 g, 0.548 mmol) was added and the mixture heated at reflux under argon overnight. The solution was cooled to room temperature, diluted with ethyl acetate (100 mL) and washed successively with water (50 mL) and brine (50 mL), dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was purified on silica gel (eluent: hexane:ether, 9:1) to give 0.910 g of 3-(2-methoxyphenyl)-4,5-methylenedioxybenzaldehyde (32%) as a white solid. 1H NMR (300 MHz; CDCl3): δ 3.84 (s, 3H); 6.07 (s, 2H); 7.00–7.10 (m, 2H); 7.31 (brs, 1H); 7.30–7.45 (m, 2H); 7.53 (brs, 1H); 9.83 (s, 1H).

Aufarbeitung

  1. customwas degassed with argon for 30 minutes
  2. temperaturethe mixture heated
  3. temperatureat reflux under argon overnight
  4. washwashed successively with water (50 mL) and brine (50 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified on silica gel (eluent: hexane:ether, 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-412485adf0d14abab96b26ca4cff8025
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153875B2

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