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Preparation of alpha-cyclopropyl carbonyl-2-benzyl-fluorobenzyl halogen

A technology of fluorobenzyl halogen and cyclopropylcarbonyl, which is applied in the field of preparation of α-cyclopropylcarbonyl-2-fluorobenzyl halogen, can solve the problems of complicated post-processing and relatively high price of N-bromosuccinimide. Expensive, unfavorable for industrial production and other problems, to achieve outstanding yield, suitable for large-scale industrial production, mild reaction conditions

Inactive Publication Date: 2012-10-10
SHANGHAI INST OF PHARMA IND CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Because this method has used extremely explosive peroxide and hypertoxic carbon tetrachloride, and N-bromosuccinimide price is more expensive, and aftertreatment is loaded down with trivial details etc. and is unfavorable for industrialized production

Method used

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  • Preparation of alpha-cyclopropyl carbonyl-2-benzyl-fluorobenzyl halogen
  • Preparation of alpha-cyclopropyl carbonyl-2-benzyl-fluorobenzyl halogen
  • Preparation of alpha-cyclopropyl carbonyl-2-benzyl-fluorobenzyl halogen

Examples

Experimental program
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Effect test

Embodiment 1

[0021] Embodiment 1: the preparation of cyclopropylcarbonyl-2-fluorobenzyl bromide

[0022] 17.8 g of cyclopropyl-2-fluorobenzyl ketone was dissolved in 100 ml of chloroform and heated to reflux, and an ethyl acetate solution of 44.7 g of copper bromide was added dropwise. After detecting the reaction until the raw materials disappeared, the cuprous bromide was filtered while it was hot and washed with chloroform, the filtrates were combined, and the solvent was evaporated to dryness to obtain 23.9 g of the target compound with a yield of 93% (HPLC showed a purity of 95.2%).

[0023] NMR (CDCl3) δppm:

[0024] 0.82-1.25 (4H, multiplet);

[0025] 2.12-2.18 (1H, multiplet);

[0026] 5.94 (1H, singlet);

[0027] 7.07-7.52 (4H, multiplet);

Embodiment 2

[0028] Embodiment 2: the preparation of cyclopropylcarbonyl-2-fluorobenzyl bromide

[0029] 17.8 g of cyclopropyl-2-fluorobenzyl ketone was dissolved in 100 ml of ethanol and heated to 60° C., and an ethanol solution of 44.7 g of copper bromide was added dropwise. Check the reaction until the raw materials disappear, filter the cuprous bromide while it is hot, and wash with ethanol, combine the filtrates, evaporate the solvent to dryness to obtain the target compound. (yield 98.5%, HPLC shows that the purity is 98.0%)

Embodiment 3

[0030] Embodiment 3: the preparation of cyclopropylcarbonyl-2-fluorobenzyl bromide

[0031] The operation is the same as in Example 2, except that tetrahydrofuran is used instead of ethanol, other conditions are the same as in Example 2, and the solvent is evaporated to dryness to obtain the product. (88.1% yield, 94.3% purity by HPLC).

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Abstract

The invention relates to the technical field of a method for preparing Alpha-cyclopropyl carbonyl-2-fluorobenzyl halogen. The method for preparing Alpha-cyclopropyl carbonyl-2-fluorobenzyl halogen is that cyclopropyl-2-fluorobenzyl ketone and a halogenating reagent react to generate the target product. The method adopts a brand-new synthesis route to prepare the cyclopropyl carbonyl-2-fluorobenzyl halogen, has mild reaction conditions and remarkable yield, does not use highly toxic and explosive raw materials and is an economical and effective method and suitable for large-scale industrialized production.

Description

technical field [0001] The invention relates to the technical field of preparation methods of α-cyclopropylcarbonyl-2-fluorobenzyl halogen. Background technique [0002] The phase III clinical trials of prasugrel have shown that it is superior to clopidogrel in terms of activity, tolerance and safety, and it is expected to become a good antithrombotic drug. Compound (II) is a key intermediate in the synthesis of prasugrel, and its existing several synthetic methods all have the disadvantages of high toxicity, high pollution, poor selectivity, and low yield. [0003] EP0542411 reports its synthetic method: [0004] [0005] (I) was dissolved in carbon tetrachloride, and the solution of bromine in carbon tetrachloride was added dropwise to obtain compound (II) after treatment. The method uses highly toxic bromine and carbon tetrachloride, and the low yield (80%) is unfavorable for industrialized production. [0006] US5288726 reports another approach: [0007] [000...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/567C07C45/63
Inventor 程兴栋童玲袁哲东沈裕辉胡志俞雄
Owner SHANGHAI INST OF PHARMA IND CO LTD
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