تفاعل #43896

معادلة التفاعل

KBr

2,4,6-trimethylphenol

4-fluorobenzonitrile

potassium carbonate

→

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

المردود 97.0%

المذيبات

toluene

NMP

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر