2-FLUORO-4-NITROBENZONITRILE synthesis
- Product Name:2-FLUORO-4-NITROBENZONITRILE
- CAS Number:34667-88-4
- Molecular formula:C7H3FN2O2
- Molecular Weight:166.11
350-32-3
34667-88-4
General procedure for the synthesis of 2-fluoro-4-nitrobenzonitrile from 2-fluoro-4-nitrobenzamide: A mixture of 2-fluoro-4-nitrobenzamide (0.83 g, 4.6 mmol) and phosphorus pentoxide/hexamethyldisiloxane in 1,2-dichloroethane (20 mL) was heated and refluxed for 4 hr at 100 °C under nitrogen atmosphere. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently filtered through a silicone plug, washed first with hexane (200 mL) and then with 5% methanol/chloroform mixture (400 mL). The methanol/chloroform washings were combined and concentrated under reduced pressure to give 2-fluoro-4-nitrobenzonitrile (0.71 g, 95% yield) as a beige solid.1H NMR (DMSO-d6) data were as follows: δ 8.46 (dd, J = 9.5, 2.0 Hz, 1H), 8.37-8.22 (m, 2H).
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Yield:-
Steps:
Multi-step reaction with 4 steps
1: 52 percent / aq. CrO3; H2SO4; AcOH / 20 - 100 °C
2: (COCl)2; DMF / tetrahydrofuran / 3 h / 0 - 20 °C
3: 15.5 g / NH3 gas / tetrahydrofuran / 2.5 h / 0 °C
4: 14.7 g / Et3N; (CF3CO)2O / tetrahydrofuran / 16 h / 20 °C
References:
Mackman;Katz;Breitenbucher;Hui;Verner;Luong;Liu;Sprengeler [Journal of Medicinal Chemistry,2001,vol. 44,# 23,p. 3856 - 3871]
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