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Preparation method of 2-fluoro-5-bromobenzaldehyde

A technology of bromobenzaldehyde and benzaldehyde, which is applied in the field of preparation of 2-fluoro-5 bromobenzaldehyde, can solve the problems of low applicability of synthesis route, increase of amplifying impurities, yield reduction, and high cost

Inactive Publication Date: 2016-08-24
SHANGHAI ZHIYAN MEDICINE TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] 2-Fluoro-5-bromobenzaldehyde is a commonly used synthetic organic raw material or pharmaceutical intermediate. WO2013037705A reports the introduction of aldehyde groups by reacting p-fluorobromobenzene and lithium diisopropylamide at a low temperature of -78°C, but the reaction process is not easy Control and enlarge the impurity to increase the yield and reduce the cost, resulting in low applicability of the synthetic route

Method used

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  • Preparation method of 2-fluoro-5-bromobenzaldehyde
  • Preparation method of 2-fluoro-5-bromobenzaldehyde

Examples

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Embodiment 1

[0008] Embodiment one: add 223ml concentrated sulfuric acid, 70g (0.56mol) o-fluorobenzaldehyde, 6g (0.045mol) anhydrous aluminum trichloride in the reactor that electric stirring is housed, thermometer and condensing tube, heat to 60 ℃ minute Add 105.5g (0.59mol) N-bromosuccinimide in batches, react for 3-8 hours, pour the system into ice water, extract with cyclohexane, wash the organic phase with water, wash with saturated brine, and anhydrous sodium sulfate Dry, filter, and concentrate to remove cyclohexane to obtain a brownish-red oil, which is collected by vacuum distillation at 63-65°C / 3mmHg fraction 91.6g, with a yield of 80% and a content of 98%.

Embodiment 2

[0009] Embodiment two: add dichloroethane and catalyzer zinc bromide 67g (0.3mol) in the reactor equipped with electric stirring, thermometer, dropping funnel and condenser, add o-fluorobenzene under stirring at 50 ℃~90 ℃ Add 62g (0.5mol) of formaldehyde, then add 80g (0.5mol) of bromine dropwise, and continue the reaction for 2-8 hours after the addition. The reaction solution was washed with water, pickled, dried and filtered over anhydrous sodium sulfate, concentrated to remove dichloroethane to obtain a brownish-red oil, and 76 g of 63-65°C / 3mmHg fraction was collected by rectification under reduced pressure, with a yield of 75% and a content of 99%.

Embodiment 3

[0010] Embodiment three: electric stirring is housed, thermometer, add 65% sulfuric acid aqueous solution 500ml, potassium bromate 167g (1mol) in the reactor of dropping funnel and condensing pipe, dropwise add o-fluorobenzaldehyde 124.1g (1mol), 90 ℃ of reactions After 2-3 hours, add 1000ml of water to the system, extract with methyl tert-butyl ether, wash the organic phase with an aqueous solution of sodium sulfite, add anhydrous sodium sulfate, dry, filter and concentrate to remove methyl tert-butyl ether to obtain a brownish-red oil, and decompress Rectification collects 63-65 ℃ / 3mmHg distillate 178g, yield 88%, content 97%.

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Abstract

The invention relates to a preparation method of 2-fluoro-5-bromobenzaldehyde as a medicine intermediate. O-fluorobenzaldehyde and a bromination reagent undergo a reaction in the presence of Lewis acid as a catalyst and the reaction product is subjected to reduced pressure distillation so that 2-fluoro-5-bromobenzaldehyde with a high yield and high content is obtained. The preparation method has the characteristics of easy availability of raw materials, less reaction processes, high yield and low cost.

Description

technical field [0001] The invention relates to a preparation method of 2-fluoro-5 bromobenzaldehyde, which is an important pharmaceutical intermediate. Background technique [0002] 2-Fluoro-5-bromobenzaldehyde is a commonly used synthetic organic raw material or pharmaceutical intermediate. WO2013037705A reports the introduction of aldehyde groups by reacting p-fluorobromobenzene and lithium diisopropylamide at a low temperature of -78°C, but the reaction process is not easy Control, amplification of impurities increases yield, high cost, resulting in low applicability of synthetic route. Contents of the invention [0003] The purpose of the invention is to overcome the existing technical defects and provide a method for preparing 2-fluoro-5 bromobenzaldehyde which is easy to get raw materials, simple in steps, mild in reaction conditions, simple in aftertreatment, low in cost and capable of scale-up production. [0004] The preparation of 2-fluoro-5 bromobenzaldehyde a...

Claims

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Application Information

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IPC IPC(8): C07C45/63C07C47/55
Inventor 王栋伟马建叶茂张基勇
Owner SHANGHAI ZHIYAN MEDICINE TECH CO LTD
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