Reaktion #46191

Reaktionsgleichung

methanol

3-chloro-4-methoxy-benzaldehyde

t-BuOK

TosMIC

→

2-(3-chloro-4-methoxyphenyl)acetonitrile

Ausbeute 83.0%

Lösungsmittel

water

THF

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGto stir for 1.5 hours at −78° C
2. 2
   SonstigeTo the cooled reaction mixture
3. 3
   TemperaturThe mixture was heated
4. 4
   Temperaturat reflux for 30 minutes
5. 5
   SonstigeSolvent of the reaction mixture was removed
6. 6
   Sonstigeto give a crude product, which
7. 7
   ExtraktionThe aqueous phase was extracted with EtOAc (20 mL×3)
8. 8
   SonstigeThe combined organic layers were dried
9. 9
   Sonstigeevaporated under reduced pressure
10. 10
    Sonstigeto give crude product, which
11. 11
    Sonstigewas purified by column chromatography (Petroleum Ether/EtOAc 10:1)

Vorschrift

To a suspension of t-BuOK (4.8 g, 40 mmol) in THF (30 mL) was added a solution of TosMIC (3.9 g, 20 mmol) in THF (10 mL) at −78° C. The mixture was stirred for 10 minutes, treated with a solution of 3-chloro-4-methoxy-benzaldehyde (1.65 g, 10 mmol) in THF (10 mL) dropwise, and continued to stir for 1.5 hours at −78° C. To the cooled reaction mixture was added methanol (10 mL). The mixture was heated at reflux for 30 minutes. Solvent of the reaction mixture was removed to give a crude product, which was dissolved in water (20 mL). The aqueous phase was extracted with EtOAc (20 mL×3). The combined organic layers were dried and evaporated under reduced pressure to give crude product, which was purified by column chromatography (Petroleum Ether/EtOAc 10:1) to afford 2-(3-chloro-4-methoxyphenyl)acetonitrile (1.5 g, 83%). 1H NMR (400 MHz, CDCl3) δ 7.33 (d, J=2.4 Hz, 1H), 7.20 (dd, J=2.4, 8.4 Hz, 1H), 6.92 (d, J=8.4 Hz, 1H), 3.91 (s, 3H), 3.68 (s, 2H). 13C NMR (100 MHz, CDCl3) δ 154.8, 129.8, 127.3, 123.0, 122.7, 117.60, 112.4, 56.2, 22.4.

Quelle