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Method for synthesizing multiple fluoro-substituted naphthalene derivative from hexafluorobenzene

A derivative and polyfluorinated technology, applied in the field of synthesis of polyfluorinated naphthalene derivatives, can solve problems such as single product substituent

Inactive Publication Date: 2007-04-25
席振峰 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] There have been many reports on the synthesis of many substituted naphthalene derivatives, but there are few examples of synthetic polyfluoronaphthalene derivatives in these reports, such as referring to the synthetic method of fluorine-free multi-substituted naphthalene derivatives: de Koning, C.B. ; Rousseau A.L.; van Otterlo, W.A.L. Tetrahedron 2003, 59, 7
In addition, some documents prepare derivatives of polyfluorinated naphthalene from partially fluorinated aromatic compounds, but the products prepared by these methods have very single substituents due to the limitation of the method. For example, see fluorine-containing naphthalene derivatives Synthetic methods: (a) Platonov, V.E.; Osina, O.I.; Maksimov, A.M.; Kolechkina, V.G.J. Fluorine Chem. 1999, 96, 191. (b) Hales, N.J.; Heaney, H.; Tetrahedron 1995, 51, 7755. (c) Brooke, G.M.; Mawson, S.D.J. Chem.Soc., Perkin Trans. 1 1990, 1919. (d) Lewis, L.N.; Uriarte, R.J.; Lewis, N.J. (e) Kim, S.H.; Matsuoka, M.; Yodoshi, T.; Kitao, T. Chem. Express 1986, 1, 129. (f) Cantrell, G.L.; Filler, R.J. Fluorine Chem. ) Gribble, G.W.; LeHoullier, C.S.; Sibi, M.P; Allen, R.W.J.Org.Chem. (i) Barlow, M.G.; Haszeldine, R.N.; Peck, C.J.J. Fluorine Chem. 1981, 18, 601. (j) Vernon, J.M.; Ahmed, M.; .(k) Gribble, G.W.; Allen, R.W.; Anderson, P.S.; Christy, M.E.; Colton, C.D. Tetrahedron letters 1976, 3673. (1) Deacon, G.B.; 1979, 182, 121

Method used

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  • Method for synthesizing multiple fluoro-substituted naphthalene derivative from hexafluorobenzene
  • Method for synthesizing multiple fluoro-substituted naphthalene derivative from hexafluorobenzene
  • Method for synthesizing multiple fluoro-substituted naphthalene derivative from hexafluorobenzene

Examples

Experimental program
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Effect test

Embodiment 1

[0029] One of the general structural formula IV class compounds (R 1 = R 2 = R 3 = R 4 =n-Et): Synthesis of 1,2,3,4-tetraethyl-5,6,7,8-tetrafluoro-naphthalene

[0030] Under the protection of an inert gas (such as high-purity nitrogen), add 1 mmol of 4,5-diethyl-3,6-diiodo-3 , 5-octadiene and 5 mL of anhydrous and oxygen-free treated THF solvent. First, the above THF solution was lowered to a lower temperature (-78°C to -55°C) with a cold bath (such as a dry ice-acetone bath), and then 4 mmol tert-butyllithium (1.6M, n-pentane solution) was added dropwise under magnetic stirring. ). After stirring the reaction at -78°C to -55°C for 1 hour, 1 mmol of hexafluorobenzene and 5 ml of DME were added. The cooling bath was removed, and the reaction solution was gradually warmed to room temperature (20°C to 28°C), stirred for 3 hours, and then washed with about 1 mL of saturated NaHCO 3Aqueous solution quenched the reaction. Extracted three times with ether (10 mL each time). ...

Embodiment 2

[0033] The second (R 1 = R 2 =n-Bu, R 3 = R 4 =Me): Synthesis of 1,2-dimethyl-3,4-dibutyl-5,6,7,8-tetrafluoro-naphthalene

[0034] The synthetic route is basically the same as above. The starting material diiodide compound for this synthesis is 5-(1-methyl-2-iodo-1-propenyl)-6-iodo-5-decene. 0.081 g of pure product was obtained (purity>98%, colorless liquid). Isolated yield 54%. The NMR and high-resolution mass spectrometry data of the compound are as follows. 1 H NMR (400MHz, CDCl 3 ): δ0.98-1.03(m, 6H), 1.51-1.55(m, 8H), 2.39(s, 3H), 2.65(d, J=7.9Hz, 3H), 2.74-2.78(m, 2H), 3.03(br,2H). 13 C NMR (400MHz, CDCl 3 ( m), 145.37(m). HRMS: calcd for C 20 h 24 f 4 340.1814, found 340.1814.

Embodiment 3

[0036] Three (R 1 = R 3 = Ph, R 2 = R 4 =n-Bu): Synthesis of 1,3-dibutyl-2,4-diphenyl-5,6,7,8-tetrafluoro-naphthalene

[0037] The synthetic route is basically the same as above. The starting material diiodide compound for this synthesis is 6-phenyl-7-(1-phenyl-1-iodo-methylene)-5-iodo-5-undecene. 0.311 g of pure product was obtained (purity>98%, colorless solid, melting point 73-74°C). Isolated yield 67%. The NMR, high-resolution mass spectrometry and elemental analysis data of the compound are as follows. 1 H NMR (400MHz, CDCl 3 ): δ0.38(t, J=7.3Hz, 3H), 0.67-0.76(m, 5H), 1.05-1.12(m, 2H), 1.18-1.24(m, 2H), 1.46-1.51(m, 2H ), 2.06-2.10(m, 2H), 2.77-2.82(m, 2H), 7.22-7.27(m, 4H), 7.36-7.45(m, 6H). 13 C NMR (400MHz, CDCl 3 ): δ12.98, 13.54, 22.72, 23.08, 31.23, 32.63(m), 34.11, 117.91(m), 119.76, 126.94, 127.19, 127.63, 128.01, 129.14, 129.17, 129.65, 132.602, 135.37 , 139.66(m), 139.94, 140.87, 142.10(m), 142.80, 144.61(m), 145.40(m). HRMS: calcd for C 30 h 28 f ...

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Abstract

The invention discloses a synthesizing method of naphthalene polyfluoride derivant synthesized by hexafluorobenzene and organic lithium compound directly, which is characterized by the following: reacting organic lithium compound by 1, 4-diiodio-1, 3-butadiene derivant and alkyl lithium; making 1, 4-diiodio-1, 3-butadiene derivant react with alkyl lithium first and hexafluorobenzene then to prepare the product.

Description

technical field [0001] The invention relates to an organic synthesis intermediate and a method for synthesizing new functional materials, in particular to a method for synthesizing polyfluoronaphthalene derivatives with various substituents. Background technique [0002] Polyfluoronaphthalene derivatives have very broad application prospects in optoelectronic materials due to their aromatic ring characteristics with partial fluorine bands. [0003] There have been many reports on the synthesis of many substituted naphthalene derivatives, but there are few examples of synthetic polyfluoronaphthalene derivatives in these reports, such as referring to the synthetic method of fluorine-free multi-substituted naphthalene derivatives: de Koning, C.B. ; Rousseau A.L.; van Otterlo, W.A.L. Tetrahedron 2003, 59, 7. In addition, some documents prepare derivatives of polyfluorinated naphthalene from partially fluorinated aromatic compounds, but the products prepared by these methods hav...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C25/22C07C17/00C07F1/02
Inventor 席振峰王志会
Owner 席振峰
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