Method for preparing o-trifluoromethylaniline compound and intermediate thereof

A technology of trifluoromethylaniline and trifluoromethylation, applied in the field of preparation of o-trifluoromethylaniline compounds, achieving high yield, mild reaction conditions and good selectivity

Active Publication Date: 2019-01-15
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] Although US 8686044 discloses the method for preparing substituted bis(trifluoromethyl)benzene (compound b, following formula) from substituted diiodobenzene (compound a), the yield (Example 3-6 in US 8686044, yield rate of 51%) is also low

Method used

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  • Method for preparing o-trifluoromethylaniline compound and intermediate thereof
  • Method for preparing o-trifluoromethylaniline compound and intermediate thereof
  • Method for preparing o-trifluoromethylaniline compound and intermediate thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0065] 1) Preparation of N-(2-iodo-6-bromo-4-heptafluoroisopropylphenyl)-2-fluoro-3-(N-methylbenzamido)benzamide (IX):

[0066]

[0067] 2-iodo-6-bromo-4-heptafluoroisopropylaniline (4.70g, 10.0mmol) was dissolved in acetonitrile (40mL), potassium iodide (0.42g, 2.5mmol) was added, and 2 -Fluoro-3-(N-methylbenzamido)benzoyl chloride (5.90 g, 20.0 mmol), heated to 85° C. for reflux reaction, monitored by TLC until the reaction was complete. The reaction solution was cooled to room temperature, filtered to remove insoluble matter, the filtrate was distilled under reduced pressure, the residue was dissolved in ethyl acetate (50 mL), washed three times with 10% sodium hydroxide solution, the aqueous phase was recovered, and the organic phase was sequentially washed with 1 mol / L Wash with hydrochloric acid and saturated brine, dry over anhydrous magnesium sulfate, filter, distill off ethyl acetate under reduced pressure, the residue is separated and purified by column chromatogr...

Embodiment 2

[0084] 1) Preparation of N-(2-iodo-6-bromo-4-heptafluoroisopropylphenyl)-2-fluoro-3-nitrobenzamide (IX):

[0085]

[0086] Dissolve 2-iodo-6-bromo-4-heptafluoroisopropylaniline (4.70g, 10.0mmol) in 40mL of acetonitrile, add potassium iodide (0.42g, 2.5mmol), and then add 2-fluoroisopropylaniline to the reaction solution -3-Nitrobenzoyl chloride (4.12g, 20.0mmol), the mixture was heated to 85°C for reflux reaction, and TLC monitored until the reaction was complete. The reaction solution was cooled to room temperature, filtered to remove insoluble matter, acetonitrile was distilled off under reduced pressure, and 50 mL of ethyl acetate was added to the residue. First, the organic phase was washed three times with 10% sodium hydroxide solution, and the aqueous phase was reclaimed, then the organic phase was washed with 1mol / L hydrochloric acid and saturated brine successively, dried over anhydrous magnesium sulfate, filtered, and ethyl acetate was distilled off under reduced p...

Embodiment 3

[0101] 1) Preparation of N-(2-iodo-6-bromo-4-heptafluoroisopropylphenyl)-2-fluoro-3-benzamidobenzamide (IX):

[0102]

[0103] Dissolve 2-iodo-6-bromo-4-heptafluoroisopropylaniline (4.70g, 10.0mmol) in N,N-dimethylformamide (40mL), add sodium iodide (0.38g, 2.5mmol ), and then added 2-fluoro-3-benzamidobenzoyl chloride (5.61g, 20.0mmol) to the reaction solution, heated to 85°C for reflux reaction, and monitored by TLC until the reaction was complete. The reaction solution was cooled to room temperature, filtered to remove insoluble matter, the filtrate was distilled under reduced pressure, the residue was dissolved in ethyl acetate (50 mL), washed three times with 10% sodium hydroxide solution, the aqueous phase was recovered, and the organic phase was sequentially washed with 1 mol / L Wash with hydrochloric acid and saturated brine, dry over anhydrous magnesium sulfate, filter, evaporate ethyl acetate under reduced pressure, and separate and purify the residue by column chr...

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Abstract

The invention belongs to the field of organic synthesis, and specifically relates to a method for preparing an o-trifluoromethylaniline compound and an intermediate thereof. The reaction formula is asshown in the specification. In the formula, each substituent group is described in the specification. Specifically, a compound VII and a compound VIII react in a suitable reaction solvent under the action of a suitable catalyst to prepare a compound IX, and the compound IX further reacts with a suitable trifluoromethylating reagent under suitable reaction conditions to prepare a compound X. The invention provides an effective preparation method for the industrial development of the insecticidal compounds.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for preparing o-trifluoromethylaniline compounds and intermediates thereof. Background technique [0002] US 8853440 discloses efficient insecticide Broflanilide (chemical name: N-[2-bromo-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-(trifluoromethyl)phenyl ]-2-fluoro-3-(N-methylbenzamido) benzamide) and the synthetic method of its analog (general formula III), as follows: [0003] [0004] In the formula: [0005] X in formula III 1 、X 3 、X 4 、X 5 , A, R 2 The definitions of and T are consistent with those in the general formula II; [0006] In general formula II, LG is selected from leaving group; T is selected from H or F; R 2 selected from H or methyl; X 1 selected from H or Cl; X 3 selected from H, F or CN; X 4 selected from H, F or CN; X 5 is H; A is selected from N or CH 2 . [0007] US 2011136878 discloses a synthetic method for the int...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/12C07C237/42C07C253/30C07C255/57
CPCC07C231/12C07C253/30C07C237/42C07C255/57
Inventor 徐靖博吴鸿飞程学明徐利保杨浩孙宁宁于海波
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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