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

HRID 2416592

Reaktionsgleichung

Reaktionsgleichung von HRID 2416592
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 μL, 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) δ 9.83 (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) δ 190.9, 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-37e15bee1d2b488ea0e7f19945ea824b
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06825185B2

Verknüpfte Notizen

Wird geladen…