Ethanol → 2-(5-Methylbenzofuran-2-yl)benzonitrile

HRID 1738

Reaktionsgleichung

Reaktionsgleichung von HRID 1738
C[O-].[Na+].C(O)C.[OH:7][C:8]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:9]=1[CH:10]=O.Br[CH2:18][C:19]1[C:20]([C:25]#[N:26])=[CH:21][CH:22]=[CH:23][CH:24]=1>CN(C)C=O.O>[C:25]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:18]1[O:7][C:8]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:9]=2[CH:10]=1)#[N:26]

Komponenten

7

Edukt 4

HCID 702EthanolHCID 69184Benzaldehyde, 2-hydroxy-5-methyl-HCID 895992-(Bromomethyl)benzonitrileHCID 10942334Sodium Methoxide2×

Produkt 1

HCID 156808442-(5-Methylbenzofuran-2-yl)benzonitrileAusbeute 63,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel3×

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A 500 mL 3-neck round bottom flask equipped with a magnetic stirrer, dropping funnel, thermometer and nitrogen bubbler was charged with 10.7 g (108 mmol) of sodium methoxide and 75 mL of absolute ethanol. A solution of 24.9 g (183 mmol) of 2-hydroxy-5-methylbenzaldehyde in 75 mL of dry dimethylformamide was added dropwise over 15 minutes. The mixture was stirred for 20 minutes then treated dropwise over 20 minutes with a solution of 34.8 g (177 mmol) of α-bromo-o-tolunitrile in 75 mL of dry dimethylformamide. The mixture was heated at 75° C. for 30 minutes, then allowed to cool for one hour. A suspension of 10.7 g (188 mmol) of sodium methoxide in 20 mL of dry dimethylformamide was added and the resulting mixture heated at 90° C. for 1.5 hours. The reaction mixture was concentrated under vacuum at 50° C. to give a brown solid that was slurried in 100-200 mL of cold water and filtered. The solids were triturated with 200 mL of methanol, filtered, washed with additional methanol, then air dried. After drying in a dessicator under high vacuum, 26.1 g (112 mmol, 63%) of the product was isolated as a beige solid. 1H NMR (200 MHz,CDCl3): 2.45 (s,3H), 7.17 (d,8 Hz,1H), 7.4 (m,3H), 7.6-7.8 (m,3H), 8.10 (d,8 Hz,1H).

Aufarbeitung

  1. customA 500 mL 3-neck round bottom flask equipped with a magnetic stirrer
  2. temperatureto cool for one hour
  3. additionwas added
  4. temperaturethe resulting mixture heated at 90° C. for 1.5 hours
  5. concentrationThe reaction mixture was concentrated under vacuum at 50° C.
  6. customto give a brown solid that
  7. filtrationfiltered
  8. customThe solids were triturated with 200 mL of methanol
  9. filtrationfiltered
  10. washwashed with additional methanol
  11. customair dried
  12. customAfter drying in a dessicator under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-6c59e00fa9b34294a8339d168dc3dcaa
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05726307

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