Reaktion #43896

Reaktionsgleichung

KBr

2,4,6-trimethylphenol

4-fluorobenzonitrile

potassium carbonate

→

4-(2,4,6-Trimethylphenoxy)benzonitrile

Ausbeute 97.0%

Lösungsmittel

toluene

NMP

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeInto a 250 mL three-necked, round-bottomed flask equipped with a magnetic stir-bar, nitrogen inlet, and a condenser
2. 2
   TemperaturThe reaction mixture was then heated
3. 3
   FiltrationThe dark solution was filtered while it
4. 4
   Temperaturwas warm
5. 5
   workup.ADDITIONthe filtrate was poured
6. 6
   workup.DISTILLATIONinto distilled water containing 5% hydrochloric acid
7. 7
   SonstigeThe solution was separated into organic layer and aqueous layer
8. 8
   workup.ADDITIONThe organic layer was diluted with dichloromethane
9. 9
   Sonstigeseparated
10. 10
    SonstigeThe solvent was removed to dryness
11. 11
    SonstigeLight brown oily residue was freeze-dried
12. 12
    Sonstigeto afford 10.1 g (97% yield)

Vorschrift

Into a 250 mL three-necked, round-bottomed flask equipped with a magnetic stir-bar, nitrogen inlet, and a condenser, 2,4,6-trimethylphenol (6.00 g, 44.1 mmol), 4-fluorobenzonitrile (5.34 g, 44.1 mmol), potassium carbonate (7.30 g, 52.8 mmol), and a mixture of NMP (100 mL) and toluene (60 mL) were placed. The reaction mixture was then heated and maintained around 140° C. for 8 h with vigorous nitrogen flow. The dark solution was filtered while it was warm and the filtrate was poured into distilled water containing 5% hydrochloric acid. The solution was separated into organic layer and aqueous layer. The organic layer was diluted with dichloromethane and separated. The solvent was removed to dryness. Light brown oily residue was freeze-dried to afford 10.1 g (97% yield): Anal. Calcd. for C16H15NO: C, 80.98%; H, 6.37%; N, 5.90%; O, 6.74%. Found: C, 80.31%; H, 6.37%; N, 5.75%; O, 6.46%. FT-IR (KBr, cm−1): 2226 (C≡N stretch). Mass spectrum (m/e): 237 (M+, 100% relative abundance), 222, 204, 194. 1H NMR (CDCl3, ppm) δ 2.05 (s, 6H, CH3), 2.30 (s, 3H, CH3), 6.81-6.84 (d, 2H, Ar), 6.91 (s, 2H, Ar), 7.53-7.56 (d, 2H, Ar). 13C NMR (CDCl3, ppm) δ 16.10, 20.79, 115.48, 129.07, 129.15, 129.88, 130.48, 134.25, 147.84, 150.03, 161.44.

Quelle