반응 #72719

반응 방정식

KHMDS

fluorobenzene

isobutyronitrile

→

objective compound

수율 50.4%

2-Methyl-2-phenylpropionitrile

수율 50.4%

용매

toluene

diethyl ether

toluene

반응 조건

후처리

1. 1
   온도to cool to room temperature
2. 2
   세척washed with water and brine
3. 3
   건조The organic fraction was dried over sodium sulfate
4. 4
   농축concentrated under reduced pressure
5. 5
   기타The product was purified by flash chromatography

실험 절차

To a solution of fluorobenzene (5.85 mL, 62.4 mmol) in 100 mL of anhydrous toluene was added isobutyronitrile (22.5 mL, 250 mmol) followed by 200 mL (100 mmol) of a 0.5 M solution of KHMDS in toluene. The reaction was stirred at 80° C. for 24 hours. The reaction was then allowed to cool to room temperature, diluted with diethyl ether, and washed with water and brine. The organic fraction was dried over sodium sulfate and concentrated under reduced pressure. The product was purified by flash chromatography using an ethyl acetate/hexanes gradient to yield 4.57 g (50%) of the objective compound as a brown oil. MS: (ESI, Pos) m/z 168.0 (M+23). 1H NMR (500 MHz, CDCl3): δ (ppm) 7.48 (d, 2H), 7.39 (t, 2H), 7.31 (t, 1H), 1.73 (s, 6H).

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