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Synthetic method of 1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene

A technology of ethoxybenzyl and iodobenzene, which is applied in the field of drug synthesis, can solve the problems of too long reaction steps, prone to danger, unfavorable large-scale production, etc., and achieve the effect of short synthetic route and favorable industrial production

Active Publication Date: 2019-01-18
NANJING REDWOOD FINE CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The above schemes all use highly corrosive acetyl chloride, which is prone to danger, and the reaction steps are too long and the yield is low, which is not conducive to large-scale production, resulting in an increase in production costs, which is not conducive to industrial production.

Method used

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  • Synthetic method of 1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene
  • Synthetic method of 1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene
  • Synthetic method of 1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] (1) Mix 5.0g of 4-bromophenetole and 100mL of tetrahydrofuran, stir until clear, and set aside.

[0030] (2) Add 0.64g of magnesium chips and 100mL of tetrahydrofuran in sequence, stir and mix thoroughly, pour 20mL of 4-bromophenetole in tetrahydrofuran into it, heat up to 45°C, stop stirring after reaching the specified temperature, and add 0.63g of elemental iodine Particles, the reaction is triggered, and bubbles overflow from the bottom of the system. When a large number of bubbles overflow, start stirring slowly until the system changes from dark red to colorless, clear and transparent, and the temperature of the system increases significantly.

[0031] (3) After adding 0.63g of elemental iodine particles, the normal rotation speed was restored, and the remaining tetrahydrofuran solution of 4-bromophenetole was added dropwise. The temperature of the system was maintained at a slight reflux state, and the dropwise addition was completed in 1-1.5 hours. After droppi...

Embodiment 2

[0035] (1) Mix 5.0g of 4-bromophenetole and 100mL of diethyl ether, and stir until clear. spare.

[0036] (2) Add 0.67g of magnesium chips and 100mL of diethyl ether in sequence, stir and mix thoroughly, pour 20mL of 4-bromophenetole ether solution into it, heat up to 50°C, stop stirring after reaching the specified temperature, and add 0.63g of elemental The iodine particles trigger the reaction, and bubbles overflow from the bottom of the system. When a large number of bubbles overflow, start stirring slowly until the system changes from dark red to colorless, clear and transparent, and the temperature of the system increases significantly.

[0037] (3) After adding 0.63g of elemental iodine particles, the normal rotation speed was restored, and the remaining ether solution of 4-bromophenetole was added dropwise. The temperature of the system was maintained at a slight reflux state, and the dropwise addition was completed in 1-1.5 hours. After dropping, keep microreflux re...

Embodiment 3

[0041] (1) Mix 5.0g of 4-bromophenetole with 100mL of a 1:1 mixed solution of diethyl ether and tetrahydrofuran, and stir until clear. spare.

[0042] (2) Add 0.69g of magnesium chips and 100mL of a mixed solution of diethyl ether and tetrahydrofuran (1:1) in sequence, start stirring and mix thoroughly, pour 20mL of 4-bromophenetole solution into it, heat up to 48°C, and reach the specified temperature , stop stirring, add 0.63g elemental iodine particles to initiate the reaction, and bubbles overflow from the bottom of the system. When a large number of bubbles overflow, start stirring slowly until the system changes from dark red to colorless, clear and transparent, and the temperature of the system increases significantly.

[0043](3) After adding 0.63g of elemental iodine particles, the normal rotation speed was restored, and the remaining 4-bromophenetole solution was added dropwise. The temperature of the system was maintained at a slight reflux state, and the dropwise ...

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Abstract

The invention belongs to the field of pharmaceutical synthesis and discloses a synthetic method of 1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene. The synthetic method comprises the following steps: (S1) dissolving 4-bromobenzene ether into a solvent, adding magnesium, and reacting under the catalysis of iodine, so as to obtain a Grignard reagent; and (S2) dissolving 2-(bromomethyl)-4-iodochlorobenzeneinto the solvent, adding the Grignard reagent prepared in the step S1, and reacting under the catalysis of cuprous iodide, so as to obtain 1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene. The method is short in synthetic route, the final product purity reaches up to 99.5%, and the yield reaches up to 95.9%, so that the method is beneficial to the industrialization production.

Description

technical field [0001] The invention relates to the technical field of medicine synthesis, in particular to a synthesis method of 1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene. Background technique [0002] Dapagliflozin is a sodium-glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes, a C-aryl glucoside compound with a chemical name: (2S, 3R, 4R, 5S, 6R)- 2-[3-(4-Ethoxybenzyl)-4-chlorophenyl]-6-hydroxymethyltetrahydro-2H-pyran-3,4,5-triol. Dapagliflozin inhibits the reabsorption of blood sugar by inhibiting renal sodium-glucose cotransporter 2, thereby regulating blood sugar levels in the body; at the same time, it can significantly reduce the level of glycosylated hemoglobin and body weight of patients. Dapagliflozin, jointly developed by Bristol-Myers Squibb and AstraZeneca, is the second SGLT2 inhibitor approved by the US FDA for the treatment of type 2 diabetes. [0003] 1-Chloro-2-(4-ethoxybenzyl)-4-iodobenzene is the key intermediate for the pr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/30C07C43/225C07F3/02
CPCC07C41/30C07C43/225C07F3/02
Inventor 吴法浩李钢高仰哲
Owner NANJING REDWOOD FINE CHEM CO LTD
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