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Chemoselectivity and Regioselectivity in Palladium Catalyzed Aromatic Cyanation of 1-Bromo-4-fluorobenzene and 4-Chlorobenzaldehyde
Chemoselectivity and Regioselectivity in Palladium Catalyzed Aromatic Cyanation of 1-Bromo-4-fluorobenzene and 4-Chlorobenzaldehyde
Journal of the Korean Chemical Society. 2012. Feb, 56(1): 175-179
Copyright © 2012, The Korean Chemical Society
  • Received : December 12, 2011
  • Accepted : January 17, 2012
  • Published : February 20, 2012
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About the Authors
영지 심
호진 이
헌철 김
순흠 박
shpark@dongguk.ac.kr

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실 험
- 촉매반응의 일반적인 실험과정
팔라듐 착물에 의한 1-bromo-4-fluorobenzene의 시안화촉매반응. Schlenk flask(10 mL)에 교반에 필요한 자석과 함께 Pd 2 (dba) 3 C 6 H 6 (5 mg, 0.005 mmol), PPh 3 (7.9 mg, 0.03 mmol), Zn(19.7 mg, 0.3 mmol), 1-bromo-4-fluorobenzene(0.028 ml, 0.25 mmol), 그리고 Zn(CN) 2 (17.7 mg, 0.151 mmol)을 넣고 DMA(3 mL)를 가한 후, 질소 기압에서 120 ℃, 4시간 동안 저어주었다. 혼합용액을 실온으로 식힌 후, Pasteur pipette을 이용하여 용액을 vial에 옮겨 담은 다음 알루미나를 약 1 cm 채운 짧은 유리관(0.7×15 cm)을 통과시키면서 diethyl ether로 용출하여 노란색의 맑은 용액을 얻었다. 이 용액을 GC/MS(MS/FID detector)로 분석하였다. 4-fluorobenzonitrile(81.4%), 부생성물인 benzonitrile(7.0%) 그리고 4,4'-difluoro-1,1'-biphenyl(11.2%)이 각각 생성되었다. For 4-fluorobenzonitrile(C 7 H 4 N 1 F 1 ): GC/MS: m/z = 121, 106, 94, 75, 63, 50, 37, 26, 14.
Acknowledgements
이 논문은 2010년도 동국대학교 연구년 지원에 의하여 이루어졌음.
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