반응 #45392

반응 방정식

3-bromo-5-fluorobenzonitrile

triethylamine

trimethylsilylacetylene

→

3-fluoro-5-((trimethylsilyl)ethynyl)benzonitrile

용매

THF

반응 조건

후처리

1. 1
   온도After an initial exotherm, the reaction was heated
2. 2
   온도at reflux for 3 hrs
3. 3
   농축The reaction mixture was concentrated on a rotary evaporator
4. 4
   workup.ADDITIONthe dark residue diluted with hexane
5. 5
   세척washed with water three times
6. 6
   여과The hexane layer was filtered through Celite
7. 7
   농축the filtrate was concentrated
8. 8
   기타to give a brown oil
9. 9
   기타The crude material was used without further purification
10. 10
    기타Ret time 3.96 min, (M+H)+=218.14

실험 절차

To a solution of commercially available 3-bromo-5-fluorobenzonitrile (5 g, 25 mmol) and triethylamine (35 ml) in 35 ml of THF was bubbled nitrogen for 10 min. Then added trimethylsilylacetylene (5.0 g, 50 mmol), copper iodide (60 mg, 0.31 mmol), and PdCl2(PPh3)2 (80 mg, 0.11 mmol) and the reaction mixture was heated with a heating mantle. After an initial exotherm, the reaction was heated at reflux for 3 hrs. The reaction mixture was concentrated on a rotary evaporator and the dark residue diluted with hexane and washed with water three times. The hexane layer was filtered through Celite and the filtrate was concentrated to give a brown oil. The crude material was used without further purification. LCMS B: Ret time 3.96 min, (M+H)+=218.14. 1H NMR, 400 MHz, CDCl3: 7.57 (s, 1H), 7.43 (m, 1H), 7.35 (m, 1H), 0.26 (s, 9H).

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