Ethanol → 4,5-Dimethoxy-2-(4-methylthiophenyl)benzaldehyde

HRID 49179

Reaktionsgleichung

Reaktionsgleichung von HRID 49179
Br[C:2]1[C:9]([O:10][CH3:11])=[C:8]([O:12][CH3:13])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:14][S:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>C1(C)C=CC=CC=1.O>[CH3:13][O:12][C:8]1[C:9]([O:10][CH3:11])=[CH:2][C:3]([CH:4]=[O:5])=[C:6]([C:19]2[CH:20]=[CH:21][C:16]([S:15][CH3:14])=[CH:17][CH:18]=2)[CH:7]=1

Komponenten

7

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 6185382-Bromo-3,4-dimethoxybenzaldehydeHCID 27339594-(Methylthio)phenylboronic acid

Produkt 1

HCID 113920804,5-Dimethoxy-2-(4-methylthiophenyl)benzaldehydeAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

2-Bromoveratraldehyde (25 g, 103.3 mmol) and 4-(methylthio)benzeneboronic acid (19.66 g, 118.5 mmol) were dissolved in toluene (550 mL) and sodium carbonate (2M, 103 mL, 206 mmol) was added. To this reaction mixture was added ethanol (50 mL) followed by tetrakis (triphenylphosphine)palladium (3.4 g, 2.5 mmol) and the reaction mixture was refluxed overnight under nitrogen atmosphere. The reaction mixture was cooled to room temperature, diluted with water (250 mL) and extracted with ethyl acetate (2×250 mL). The combined organic extracts were washed with water (4×250 mL), brine (1×250 mL), dried over sodium sulfate, filtered and the filtrate was evaporated under reduced pressure to give the crude product. The product was purified by trituration with ethyl acetate/hexane to give the title compound as a white solid (21.3 g, 85% yield), mp 114-115° C. 1H NMR (CDCl3, 300 MHz) δ9.83 (s, 1H), 7.64 (s, 1H), 7.43-7.23 (m, 4H), 6.83 (s, 1H), 3.98 (d, J=2.4 Hz, 6H), 2.55 (s, 3H). 13C NMR (CDCl3, 75.45 MHz) δ190.9, 153.4, 148.7, 1408, 138.9, 134.5, 134.1, 130.5, 130.1, 128.0, 128.0, 126.9, 126.1, 112.5, 108.7, 56.2, 56.1, 15.6. LRMS (APIMS) m/z 289 (M+H)+.

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed overnight under nitrogen atmosphere
  2. extractionextracted with ethyl acetate (2×250 mL)
  3. washThe combined organic extracts were washed with water (4×250 mL), brine (1×250 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe filtrate was evaporated under reduced pressure
  7. customto give the crude product
  8. customThe product was purified by trituration with ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-12d70e5dc7a843fcae2bd945d35205be
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706724B2

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