Reaktion #45392

Reaktionsgleichung

3-bromo-5-fluorobenzonitrile

triethylamine

trimethylsilylacetylene

→

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

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter an initial exotherm, the reaction was heated
2. 2
   Temperaturat reflux for 3 hrs
3. 3
   EinengenThe reaction mixture was concentrated on a rotary evaporator
4. 4
   workup.ADDITIONthe dark residue diluted with hexane
5. 5
   Waschenwashed with water three times
6. 6
   FiltrationThe hexane layer was filtered through Celite
7. 7
   Einengenthe filtrate was concentrated
8. 8
   Sonstigeto give a brown oil
9. 9
   SonstigeThe crude material was used without further purification
10. 10
    SonstigeRet time 3.96 min, (M+H)+=218.14

Vorschrift

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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