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Preparation method of 2-fluoro-3-iodoaniline

A technology of iodoaniline and fluoroiodine, which is applied in the field of preparation of 2-fluoro-3-iodoaniline, can solve the problems of complex products, difficulty in controlling reaction conditions, and many by-products of iodine removal, so as to achieve cheap and easy-to-obtain raw materials and avoid product Decomposition, the effect of improving yield and product purity

Inactive Publication Date: 2013-08-14
苏州科捷生物医药有限公司
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0007] The results show that the reduction with zinc powder, iron powder, Raney-Ni-hydrazine hydrate, sodium hydrosulfite, etc., produces complex products; catalytic hydrogenation with Raney-Ni, palladium carbon, etc., more iodine by-products, it is difficult to control the reaction conditions, a large amount of preparation especially when

Method used

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  • Preparation method of 2-fluoro-3-iodoaniline
  • Preparation method of 2-fluoro-3-iodoaniline
  • Preparation method of 2-fluoro-3-iodoaniline

Examples

Experimental program
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Embodiment 1

[0018] Embodiment 1: Synthesis of 2-fluoro-3-iodobenzoic acid (compound 2)

[0019]

[0020] Diisopropylamine (13 ml, 91.0 mmol) was dissolved in tetrahydrofuran (100 ml), and 2.5M n-butyllithium solution (36.4 ml, 91.0 mmol) was added dropwise at -20°C under nitrogen protection. After dropping, stir at 0°C for 30 minutes. Then, a solution of o-fluoroiodobenzene (18.4 g, 82.8 mmol) in tetrahydrofuran (50 mL) was added dropwise, and stirring was continued at -70°C for 1 hour. Dry ice (50 g) was added, allowed to warm to room temperature and stirred overnight. 100 ml of water was added to the above reaction mixture, and the organic phase was separated. The aqueous phase was acidified with concentrated hydrochloric acid to pH 1-2, extracted three times with ethyl acetate, and dried over anhydrous sodium sulfate. Concentration under reduced pressure afforded 15.5 g of yellow solid (2), yield: 70.5%.

Embodiment 2

[0021] Example 2: Synthesis of tert-butyl 2-fluoro-3-iodophenylcarbamate (compound 3)

[0022]

[0023] Compound (2) (13.3g, 50.0mmol), triethylamine (20.8ml, 150.0mmol) and DPPA (26.7g, 100.0mmol) were dissolved in tert-butanol (50ml) and toluene (50ml), Heat to 80°C and stir overnight. Distilled under reduced pressure, the residue was subjected to silica gel column chromatography (200-300 mesh, petroleum ether: ethyl acetate = 100:1-20:1), and vacuum-dried to obtain 9.31 g of colorless liquid (3), yield: 55.3% .

Embodiment 3

[0024] Embodiment 3: Synthesis of 2-fluoro-3-iodoaniline (compound 4)

[0025]

[0026] Compound (3) (9.31 g, 27.7 mmol) was dissolved in methanol (50 mL), concentrated hydrochloric acid (10 mL) was added, and stirred at room temperature for 3 hours. The methanol was distilled off under reduced pressure, and the saturated sodium bicarbonate solution was basified to pH 8-9. Extracted with ethyl acetate, dried over anhydrous sodium sulfate. Concentration under reduced pressure afforded 6.6 g of off-white solid (4), yield: 100%.

[0027] 1 H-NMR (DMSO-d 6 , 400MHz): δ6.35~6.49 (2H, m), δ7.01 (1H, d), δ4.19 (2H, brs).

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Abstract

The invention discloses a preparation method of 2-fluoro-3-iodoaniline. A target compound is obtained by introducing carboxyl by taking o-fluoroiodobenzene as a starting material, then carrying out rearrangement and finally removing-BOC. The method is simple and convenient, is easy to operate and is suitable for large-scale preparation.

Description

technical field [0001] The invention relates to a preparation method of 2-fluoro-3-iodoaniline, belonging to the technical fields of medicine and chemical industry. Background technique [0002] Aniline is one of the most important intermediates in the dye industry, which can be used in the manufacture of acid ink blue G, acid medium BS, acid bright yellow, direct orange S, direct pink, indigo, disperse yellow brown, cationic pink FG and active Brilliant red X-SB, etc.; used in the manufacture of golden red, golden red g, big red powder, phenol cyanine red, oil-soluble black, etc. in organic pigments. In the printing and dyeing industry, it is used to dye nigrosine; in the pesticide industry, it is used to produce many insecticides and fungicides such as DDV, bifen, and toxachlor; aniline is an important raw material for rubber additives, and is used to manufacture anti-aging agents A Anti-aging agent D, anti-aging agent RD and anti-aging agent 4010, accelerators M, 808, D ...

Claims

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Application Information

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IPC IPC(8): C07C211/52C07C209/62
Inventor 邵东邵文祺
Owner 苏州科捷生物医药有限公司
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