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Preparation method of boscalid intermediate 2-(4-chlorophenyl)nitrobenzene

A technology of boscalid and o-chloronitrobenzene, applied in the field of pesticides, can solve the problems of poor operability, complex process, high cost of raw materials, and achieve the effects of low environmental protection pressure, simple process flow, and shortened reaction time

Active Publication Date: 2017-02-15
JINGBO AGROCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] The purpose of the present invention is to provide a novel synthesis process, solve the problems of complex traditional process, poor operability and high raw material cost of boscalid intermediates, realize a truly simplified process flow, reduce manufacturing costs and labor, Improve content and yield

Method used

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  • Preparation method of boscalid intermediate 2-(4-chlorophenyl)nitrobenzene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Under nitrogen protection, in a 250mL four-necked round-bottomed flask, magnesium chips (2.88g, 0.12mol), 10mL of anhydrous tetrahydrofuran, 15mL of toluene, 1.8% p-chlorobromobenzene (0.35 g, 0.0018mol) and 0.01g of iodine, stir slowly at 20-25°C and wait for initiation. After the system is initiated, the temperature rise is completed. Adjust the system temperature to 40-50°C, and slowly add p-chlorobromobenzene (18.9g, 0.0982 mol) and a mixture of 20mL tetrahydrofuran and 20mL toluene. The Grignard reagent was prepared after about 4 hours of reaction. The yield measured by acid titration (calculated as p-chlorobromobenzene) was 97.5%.

[0036] Under nitrogen protection, the Grignard reagent solution prepared above was slowly added dropwise to a solution of 30 mL of tetrahydrofuran, o-chloronitrobenzene (17.59 g, 0.11 mol), 0.539 g of anhydrous NiCl2 and 3.66 g of P(Ph)3. The reaction temperature is kept at 40-45°C. After the Grignard reagent is slowly added, the rea...

Embodiment 2

[0038] Under nitrogen protection, add zinc powder (7.816g, 0.12mol), 20mL of anhydrous tetrahydrofuran, p-chlorobromobenzene (0.35g, 0.0018 mol) and 0.02g of iodine, stirred slowly at 25-30°C and waited for initiation. After the system was initiated and the temperature rise was completed, adjust the temperature of the system to 50-60°C, and slowly add p-chlorobromobenzene (18.9g, 0.0982mol) and 40mL of tetrahydrofuran dropwise of the mixture. The reaction is about 4h to obtain the zinc reagent. The yield measured by acid titration (calculated as p-chlorobromobenzene) was 97.5%. Under nitrogen protection, the zinc reagent solution prepared above was slowly added dropwise to a solution of 30 mL of tetrahydrofuran, o-chloronitrobenzene (17.59 g, 0.11 mol), 0.539 g of anhydrous NiCl2 and 3.66 g of P(Ph)3. The reaction temperature is maintained at 45-50°C. After the Grignard reagent is slowly added, the gas-phase detection format reagent remains less than 0.5%, and the zinc reage...

Embodiment 3

[0040]Under nitrogen protection, add zinc powder (9.77g, 0.15mol), 10mL anhydrous tetrahydrofuran, 15mL toluene, p-chlorobromobenzene (0.318 g, 0.00165mol) and 0.015g iodine, stirred slowly at 20-25°C and waited for initiation. After the system was initiated and the temperature rise was completed, adjust the system temperature to 40-50°C, and slowly add p-chlorobromobenzene (18.93g, 0.0983mol) dropwise and 40mL tetrahydrofuran mixture. The Grignard reagent was prepared after about 3 hours of reaction. The yield measured by acid titration (calculated as p-chlorobromobenzene) was 98.1%. Under nitrogen protection, the Grignard reagent solution prepared above was slowly added dropwise to a solution of 35 mL THF, o-chloronitrobenzene (18.39 g, 0.115 mol), 0.577 g anhydrous NiCl2 and 3.46 g P(Ph)3. The reaction temperature is maintained at 35-45°C. After the Grignard reagent is slowly added, the remaining gas phase detection format reagent is less than 0.5%, and the zinc reagent i...

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Abstract

The invention belongs to the technical field of pesticides, relates to preparation technology of agricultural bactericide intermediates, and especially relates to preparation technology of 2-(4-chlorophenyl)nitrobenzene. 4-bromochlorobenzene and 2-nitrochlorobenzene are used as raw materials, at least Grignard reaction, catalytic coupling, and after treatment are carried out, and the preparation technology is characterized in that benzenes, ethers or tetrahydrofuran and a mixed solvent thereof are used as solvents, and the catalytic coupling reaction is carried out with catalysis of Ni and PPh3 and protection of nitrogen or inert gas; the heterogeneous catalytic reaction process has fast speed, catalyst amount used in the reaction is obviously reduced, reaction time is substantially shortened, and overall yield is more than 90%.

Description

[0001] Technical field: [0002] The invention belongs to the technical field of pesticides, and relates to the preparation technology of agricultural fungicide intermediates, in particular to the preparation technology of boscalid intermediate: 2-(4-chlorophenyl)nitrobenzene. [0003] Background technique: [0004] Boscalid is an important new fungicide with no cross-resistance with other drugs, safe and beneficial ecological effects and toxicological data on crops. [0005] Chemical name: 2-chloro-N-(4-chlorobiphenyl-2-yl)nicotinamide [0006] Molecular formula: C 18 h 12 Cl 2 N 2 o [0007] Relative molecular mass (according to the international relative atomic mass in 2005): 343.21 [0008] Structural formula: [0009] [0010] Boscalid is a new type of nicotinamide systemic fungicide developed by BASF, Germany. It is an inhibitor of succinate coenzyme Q reductase in the mitochondrial respiratory chain. It mainly controls many diseases such as powdery mildew, gra...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/12C07C205/12
CPCC07C17/35C07C201/12C07C205/12C07C25/06
Inventor 宫薇薇韦能春鲍洪涛王杰秀逄廷超
Owner JINGBO AGROCHEM TECH CO LTD
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