4-Fluoronitrobenzene is an organic compound with the formula FC6H4NO2. It is one of three isomeric fluoronitrobenzenes.[2] A yellow oil, it is prepared from 4-nitrochlorobenzene using the Halex process:

O2NC6H4Cl + KF → O2NC6H4F + KCl

4-Fluoronitrobenzene can be hydrogenated to give 4-fluoroaniline,[3] which is a precursor to the fungicide fluoroimide [de] and parafluorofentanyl.

Owing to the presence of the electron withdrawing nitro group, the fluoride is a good leaving group in fluoronitrobenzenes. Thus reaction with phenoxide gives the mononitrodiphenylether.[4]

References

  1. ^ "1-Fluoro-4-nitrobenzene". pubchem.ncbi.nlm.nih.gov.
  2. ^ Gerald Booth, "Nitro Compounds, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH: Weinheim, 2005. doi:10.1002/14356007.a17_411
  3. ^ Jagadeesh, Rajenahally V.; Surkus, Annette-Enrica; Junge, Henrik; Pohl, Marga-Martina; Radnik, Jörg; Rabeah, Jabor; Huan, Heming; Schünemann, Volker; Brückner, Angelika; Beller, Matthias (2013). "Nanoscale Fe2O3-Based Catalysts for Selective Hydrogenation of Nitroarenes to Anilines". Science. 342 (6162): 1073–1076. Bibcode:2013Sci...342.1073J. doi:10.1126/science.1242005. PMID 24288327. S2CID 11780985.
  4. ^ Brewster, Ray Q.; Groening, Theodore (1934). "p-Nitrodiphenyl Ether". Organic Syntheses. 14: 66. doi:10.15227/orgsyn.014.0066.
Allikas: http://en.wikipedia.org/wiki/4-Fluoronitrobenzene
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