Реакция #43896

Уравнение реакции

KBr

2,4,6-trimethylphenol

4-fluorobenzonitrile

potassium carbonate

→

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

Выход 97.0%

Растворители

toluene

NMP

Условия реакции

Обработка

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

Методика

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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