반응 #43896

반응 방정식

KBr

2,4,6-trimethylphenol

4-fluorobenzonitrile

potassium carbonate

→

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

수율 97.0%

용매

toluene

NMP

반응 조건

후처리

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

실험 절차

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.

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