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Preparation of fluorinated anilines

A technology of fluoride and compound, which is applied in the field of preparation of fluorinated aniline, can solve the problems such as unusable

Inactive Publication Date: 2008-06-25
SALTIGO GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this approach generally cannot be used when the nitrobenzene is more highly chlorinated or there are substituents that activate the nitro group for the Halex reaction (see Tetrahedron, 1995, 55, 7725-7738; J. Am. Chem. Soc.1956, 78, 6034)

Method used

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  • Preparation of fluorinated anilines
  • Preparation of fluorinated anilines
  • Preparation of fluorinated anilines

Examples

Experimental program
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Effect test

Embodiment 1

[0076] Preparation of 2,2',4,4',6,6'-hexafluoroazobenzene

[0077] In the absence of moisture, initially 4.3 g of dry potassium fluoride and 3.0 g of 2,2',4,4',6,6'-hexachloroazobenzene were added to 51 g of sulfolane, and 0.2 g of bromide Tetraphenylphosphonium. Subsequently, the mixture was heated to 180° C. and stirred for 12 hours. After cooling, the mixture was drained into 150 ml of water and extracted twice with 50 ml of cyclohexane (each). After crystallization, 1.7 g (76% of theory) of the desired product were obtained.

Embodiment 2

[0079] Preparation of 2,4,6-trifluoroaniline

[0080] 2,2',4,4',6,6'-hexafluoroazobenzene of 1.0g Example 1 was dissolved in 20ml methanol at room temperature, and 0.6g ammonium formate and 0.5g zinc powder were added continuously. The mixture was stirred at room temperature for 1 hour. The starting material was completely converted by GC analysis. After methanol had been distilled off, 2,4,6-trifluoroaniline was extracted in cyclohexane and dried, and the solvent was distilled off again. This leaves 0.9 g of the desired product (89% of theory).

Embodiment 3

[0082] Preparation of 2,2'-bis(trifluoromethyl)-4,4'-difluoroazobenzene

[0083] In the same manner as in Example 1, 9.8 g of 2,2'-bis(trifluoromethyl)-4,4'-dichloroazobenzene, 4 g of potassium fluoride and 0.5 g tetraphenylphosphonium bromide was reacted for 15 hours. After crystallization, 5.8 g of 2,2'-bis(trifluoromethyl)-4,4'-difluoroazobenzene (65% of theory) were obtained.

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Abstract

The invention relates to a process for preparing fluorinated anilines starting from the corresponding chlorinated anilines, and also to the use of the fluorinated anilines.

Description

technical field [0001] The present invention relates to a method for preparing fluorinated anilines from corresponding chlorinated anilines, and also relates to the application of fluorinated anilines. technical background [0002] Fluorinated anilines are important intermediates for the preparation of active pharmaceutical ingredients and agrochemicals, as described in particular in WO-A98 / 46607 and WO 98 / 46608. [0003] Known methods for their preparation include, for example, nitration of fluorinated aromatic hydrocarbons and subsequent reduction of the nitro compound to the corresponding aniline. In this way, for example, 4-fluoroaniline and 2,4-difluoroaniline can be prepared from fluorobenzene and 1,3-difluorobenzene, respectively (see J.Org.Chem., 1962, 27, 1910- 11; J. Fluor. Chem., 2002 113(2), 207-9). The disadvantage of this method is that the fluorinated arenes are expensive and the nitration step allows only limited substitution patterns on the aromatic rings....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C209/42C07C211/52C07B61/00C07C245/08
CPCC07C211/52C07C245/08C07C209/42
Inventor M·米库拉斯A·马胡尔德
Owner SALTIGO GMBH
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