反応 #45392

反応方程式

3-bromo-5-fluorobenzonitrile

triethylamine

trimethylsilylacetylene

→

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

溶媒

THF

反応条件

後処理

1. 1
   温度After an initial exotherm, the reaction was heated
2. 2
   温度at reflux for 3 hrs
3. 3
   濃縮The reaction mixture was concentrated on a rotary evaporator
4. 4
   workup.ADDITIONthe dark residue diluted with hexane
5. 5
   洗浄washed with water three times
6. 6
   ろ過The hexane layer was filtered through Celite
7. 7
   濃縮the filtrate was concentrated
8. 8
   その他to give a brown oil
9. 9
   その他The crude material was used without further purification
10. 10
    その他Ret time 3.96 min, (M+H)+=218.14

実験手順

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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