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Method for synthesizing 2-chloro-3-fluorobromobenzene

A synthesis method and fluorobromobenzene technology are applied in the field of synthesis of 2-chloro-3-fluorobromobenzene, can solve problems such as lack of synthesis route, reaction condition yield, physical and chemical constants, etc., and achieve low difficulty in treating three wastes and safe operation , the effect of mild reaction conditions

Active Publication Date: 2011-04-06
CHANGZHOU XIAOGUO INFORMATION SERVICES
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  • Description
  • Claims
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Problems solved by technology

[0003] For the research on the synthesis method of 2-chloro-3 fluorobromobenzene, 1-bromo-2,3 -Dichlorobenzene or 2-bromo-1,3-dichlorobenzene and other similar structure compounds (WO 2009103440A1, WO 2009103439A1, WO 2008120761A1, CN 101528034 A, WO 2006053024A2) are mentioned, but for 2-chloro The description of the synthesis method of -3-fluorobromobenzene lacks data such as its specific synthesis route, reaction conditions, yield and physical and chemical constants

Method used

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  • Method for synthesizing 2-chloro-3-fluorobromobenzene

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Embodiment 1

[0019] (1) Pour 100 mL of DMF into a dry 500 mL four-necked bottle, add 58.2 g of 3-chloro-2-fluoroaniline under stirring, cool down to 0~10 °C after it is completely dissolved, and then add 71.5 g of NBS , GC tracking detection, when the content of the raw material 3-chloro-2-fluoroaniline drops to 1-2%, the bromination reaction is completed;

[0020] (2), pour the mixture prepared in step (1) into 500mL ice-water mixture, separate the oil layer, wash the oil layer twice with 100mL cold water respectively, filter with suction, and separate out light yellow granular solid, after drying Weighed to obtain 86.5g of 4-bromo-3-chloro-2-fluoroaniline, with a content of 98.425% (GC), and a molar yield of 96.3% (based on 3-chloro-2-fluoroaniline), with a melting range of 51.2~53.7℃. 1 HNMR (CDCl 3 ), δ: 6.58 ( s , 1H, Ar-H), 7.16 ( m , 1H, Ar-H), 3.80 ( m , 2H, -NH 2 ); MS, m / Z: 223 (molecular ion peak), 144, 117, 108, 91, 81;

[0021] (3), pour 250g of sulfuric acid with a con...

Embodiment 2

[0024] (1) Pour 250 mL of DMF into a dry 1L four-necked bottle, add 146.0g of 3-chloro-2-fluoroaniline under stirring, cool down to 0~10°C after it is completely dissolved, add 180g of NBS, GC Follow up and detect, when the content of the raw material 3-chloro-2-fluoroaniline drops to 1-2%, the bromination reaction ends;

[0025] (2), pour the mixture obtained in step (1) into 1000mL ice-water mixture, separate the oil layer, wash the oil layer 3 times with 200mL cold water respectively, filter with suction, and separate out light yellow granular solid, after drying Weighed to obtain 219.0g of 4-bromo-3-chloro-2-fluoroaniline, the content was 98.672% (GC), and the molar yield was 97.6% (based on 3-chloro-2-fluoroaniline), and the melting range was 52.0~53.6℃. 1 HNMR (CDCl 3 ), δ: 6.58 ( s , 1H, Ar-H), 7.14 ( m , 1H, Ar-H), 3.81 ( m , 2H, -NH 2 ); MS, m / Z: 223 (molecular ion peak), 144, 117, 108, 91, 81;

[0026] (3), pour 700g of sulfuric acid with a concentration of 50...

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Abstract

The invention relates to a method for synthesizing 2-chloro-3-fluorobromobenzene. The synthesizing method comprises the following steps of: performing bromination reaction on 3-chloro-2-fluoroaniline serving as a raw material and N-bromosuccinimide serving as a bromination reagent to introduce -Br on the para-position of the -NH2 in the 3-chloro-2-fluoroaniline so as to generate 4-brono-3-chloro-2-fluoroaniline, and then performing diazotization amino removal reduction reaction on sodium nitrite, isopropanol and cuprous chloride serving as raw materials to obtain the 2-chloro-3-fluorobromobenzene. The method has the advantages of mild conditions of the synthesis reaction, convenience of operation and control and relatively low three-waste pressure, and is favorable for industrialized production.

Description

technical field [0001] The present invention relates to a kind of synthetic method of the medicine intermediate that can be used as anticancer enzyme inducer and a kind of medicine intermediate that can be used as oxytocin receptor antagonist, especially a kind of synthesis of 2-chloro-3-fluorobromobenzene method. Background technique [0002] The English name of 2-chloro-3-fluorobromobenzene is 2-Chloro-3-fluorobromobenzene, and the molecular formula is C 6 h 3 BrClF is a pharmaceutical intermediate, which can be used to synthesize an intermediate of an anticancer enzyme inducer and an intermediate of an oxytocin receptor antagonist, and can also be used to synthesize a pharmaceutical intermediate 2-chloro-3-fluorobenzene formaldehyde. [0003] For the research on the synthesis method of 2-chloro-3 fluorobromobenzene, 1-bromo-2,3 -Dichlorobenzene or 2-bromo-1,3-dichlorobenzene and other similar structure compounds (WO 2009103440A1, WO 2009103439A1, WO 2008120761A1, CN 1...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C25/13C07C17/35
Inventor 赵昊昱薛叙明
Owner CHANGZHOU XIAOGUO INFORMATION SERVICES
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