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Md. D. Hossain et al.
SHORT PAPER
4-Fluoro-1-iodobenzene23
Yield: 0.167 g (72%).
1H NMR (300 MHz, CDCl3): d = 7.64–7.59 (m, 2 H, ArH), 6.86–
6.80 (m, 2 H, ArH).
13C NMR (75 MHz, CDCl3): d = 162.68 (d, J = 245.4 Hz, CF),
138.93 (d, J = 7.4 Hz, CCCF), 117.74 (d, J = 21.7 Hz, CCF), 86.91
(d, J = 3.1 Hz, CCCCF).
Rappoport, Z., Eds.; Wiley-Interscience: Chichester, 1995,
535. (e) Steel, P. G. In Rodd’s Chemistry of Carbon
Compounds, Part 1, 2nd ed., Vol. 3; Sainsbury, M., Ed.;
Elsevier: Amsterdam, 1996, 178.
(2) Krassowska-Swiebocka, B.; Lulinski, P.; Skulski, L.
Synthesis 1995, 926.
(3) Lulinski, P.; Skulski, L. Bull. Chem. Soc. Jpn. 1997, 70,
1665.
(4) Lulinski, P.; Skulski, L. Bull. Chem. Soc. Jpn. 1999, 72, 115.
(5) Shimizu, A.; Yamataka, K.; Isoya, T. Bull. Chem. Soc. Jpn.
1985, 58, 1611.
(6) Lulinski, P.; Skulski, L. Bull. Chem. Soc. Jpn. 2000, 73, 951.
(7) Kryska, A.; Skulski, L. J. Chem. Res., Synop. 1999, 590.
(8) Barluenga, J.; Campos, P. J.; González, J. M.; Asensio, G.
Chem. Soc., Perkin Trans. 1 1984, 2623.
(9) Agnieszka, Z. A.; Skulski, L. Molecules 2005, 10, 1307.
(10) Sathiyapriya, R.; Karunakaran, R. J. E-J. Chem. 2006, 3, 65.
(11) Yang, S. G.; Kim, Y. H. Tetrahedron Lett. 1999, 40, 6051.
(12) Noda, Y.; Kashima, M. Tetrahedron Lett. 1997, 38, 6225.
(13) Rozen, S.; Zamir, D. J. Org. Chem. 1990, 55, 3552.
(14) Shellhamer, D. F.; Jones, B. C.; Pettus, B. J.; Pettus, T. L.;
Stringer, J. M.; Heasley, V. L. J. Fluorine Chem. 1998, 88,
37.
(15) Zupan, M.; Iskra, J.; Stavber, S. Tetrahedron Lett. 1997, 38,
6305.
(16) Bradzil, L. C.; Cutler, C. J. J. Org. Chem. 1994, 59, 6233.
(17) Sy, W.-W. Tetrahedron Lett. 1993, 34, 6223.
(18) Bachky, A.; Foubelo, F.; Yus, M. Tetrahedron 1994, 50,
5139.
(19) Hossain, M. D.; Kitamura, T. Tetrahedron Lett. 2006, 47,
7889.
(20) Hossain, M. D.; Ikegami, Y.; Kitamura, T. J. Org. Chem.
2006, 71, 9903.
1,4-Diiodobenzene
Yield: 0.253 g (73%); mp 127–128 °C (Lit.22 mp 129 °C).
1H NMR (300 MHz, CDCl3): d = 7.39 (s, 4 H, ArH).
13C NMR (75 MHz, CDCl3): d = 138.26, 93.35.
3-Trifluoromethyl-1-iodobenzene22
Yield: 0.170 g (60%).
1H NMR (300 MHz, CDCl3): d = 7.95 (s, 1 H, ArH), 7.88 (d, J = 7.8
Hz, 1 H, ArH), 7.58 (d, J = 7.8 Hz, 1 H, ArH), 7.22 (t, J = 7.8 Hz,
1 H, ArH).
13C NMR (75 MHz, CDCl3): d = 140.85, 134.29 (q, J = 3.7 Hz,
CCCF), 132.37 (q, J = 32.8 Hz, CCF), 130.35, 124.50 (q, J = 3.7
Hz, CCCF), 122.92 (q, J = 270.7 Hz, CF), 93.82.
3-Iodobenzoic Acid
Yield: 0.164 g (65%); mp 185–186 °C (Lit.22 mp 187–188 °C).
1H NMR (300 MHz, CDCl3): d = 8.34 (s, 1 H, ArH), 8.00 (d, J = 8.1
Hz, 1 H, ArH), 7.90 (d, J = 8.1 Hz, 1 H, ArH), 7.25 (t, J = 8.1 Hz,
1 H, ArH).
13C NMR (75 MHz, CDCl3): d = 168.01, 142.80, 139.58, 133.90,
131.23, 129.85, 94.35.
(21) Lulinski, P.; Kryska, A.; Sosnowski, M.; Skulski, L.
Synthesis 2004, 441.
(22) Dictionary of Organic Compounds, 6th ed.; Chapman &
Hall: London, 1996.
(23) Lulinski, P.; Krassowska-Swiebocka, B.; Skulski, L.
Molecules 2004, 9, 595.
References
(1) Reviews on aromatic iodination: (a) Roedig, A. In Houben-
Weyl, Methoden der organischen Chemie, 4th ed., Vol. 5/4;
Mueller, E., Ed.; Thieme: Stuttgart, 1960, 517.
(b) Merkushev, E. B. Usp. Khim. 1984, 53, 583; Russ. Chem.
Rev. (Engl. Transl.); 1984, 53, 343. (c) Merkushev, E. B.
Synthesis 1988, 923. (d) Sasson, Y. In The Chemistry of
Halides, Pseudohalides and Azides, Suppl. D1; Patai, S.;
Synthesis 2008, No. 5, 690–692 © Thieme Stuttgart · New York