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A kind of preparation method of 1-(7-bromobenzo[d][1,3]dioxol-4-yl)ethan-1-one

A technology of dioxole and bromobenzo, which is applied in the field of preparation of 1-ethan-1-one, can solve the problems of low product purity, low yield, long synthetic route, etc., and achieve improved yield and purity Effect

Active Publication Date: 2022-07-29
阜阳欣奕华制药科技有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, in the related art, the synthetic route of 1-(7-bromobenzo[D][1,3]dioxol-4-yl)ethan-1-one is long, the yield is low, and the product purity is low. Low

Method used

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  • A kind of preparation method of 1-(7-bromobenzo[d][1,3]dioxol-4-yl)ethan-1-one
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  • A kind of preparation method of 1-(7-bromobenzo[d][1,3]dioxol-4-yl)ethan-1-one

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preparation example Construction

[0022] Preparation of compound represented by formula (II)

[0023]

preparation example 1

[0025] Add the compound piperonyl ring (136.0g, 1.114mol) and 200mL of tetrahydrofuran represented by the formula (I) into the reactor, cool down to below -78°C, add n-butyllithium (135.0g, 2.107mol) dropwise, keep at -79°C The reaction was carried out for 1.5h; after that, acetyl chloride (96.3g, 1.226mol) was added dropwise and the temperature of the dropwise addition was kept below -79°C, then the temperature was slowly raised to 20-30°C, and the reaction was maintained for 1.5h. The reaction droplets were added to 150 mL of water for quenching and the quenching temperature was kept below 35 °C, and then H with a concentration of 10% by weight was successively used. 2 SO 4 100 mL of aqueous solution, 200 mL of saturated brine, and 200 mL of water were washed once, and the compound of formula (II) (171.87 g, 1.047 mol, yield 93.97%) was obtained by liquid separation.

preparation example 2

[0027] The compound piperonyl ring (136g, 1.114mol) and 200mL of tetrahydrofuran represented by formula (I) were added to the reactor, cooled to below -78°C, and n-butyllithium (135g, 2.107mol) was added dropwise, and the reaction was incubated at -79°C for 1.5 h. Acetyl chloride (104.8 g, 1.336 mol) was added dropwise, and the temperature of the dropwise addition was kept below -79°C, then the temperature was slowly raised to 20-30°C, and the reaction was maintained for 1.5 h. The reaction droplets were added to 150 mL of water for quenching, and the quenching temperature was kept below 35 °C; 2 SO 4 100 mL of aqueous solution, 200 mL of saturated brine, and 200 mL of water were each washed once, and then separated to obtain the compound represented by formula (II) (169.0 g, 1.029 mol, yield 92.40%).

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Abstract

The application relates to the technical field of organic synthesis, and specifically discloses a preparation method of 1-(7-bromobenzo[D][1,3]dioxol-4-yl)ethan-1-ketone, Using piperonyl ring as the starting material, acylation reaction, carbonyl protection reaction, bromination reaction and carbonyl deprotection reaction are carried out in sequence to obtain 1-(7-bromobenzo[D][1,3]dioxolane alken-4-yl)ethan-1-ketone. The present application not only simplifies the synthetic route, but also improves the yield and purity.

Description

technical field [0001] The present application relates to the technical field of organic synthesis, and more particularly, to a kind of 1-(7-bromobenzo[D][1,3]dioxol-4-yl)ethan-1-one preparation method. Background technique [0002] 1-(7-Bromobenzo[D][1,3]dioxol-4-yl)ethan-1-one (CAS: 1892297-18-6) is an important intermediate in drug synthesis, For example: chronic hepatitis C treatment drug - Clopavir Hydrochloride (ClopavirHydrochloride). [0003] However, the synthesis route of 1-(7-bromobenzo[D][1,3]dioxol-4-yl)ethan-1-one in the related art is long, the yield is low, and the product purity Low. SUMMARY OF THE INVENTION [0004] In order to simplify the synthetic route and improve the yield and purity, the present application provides a 1-(7-bromobenzo[D][1,3]dioxol-4-yl)ethan-1-one The preparation method adopts the following technical scheme: [0005] A preparation method of compound 1-(7-bromobenzo[D][1,3]dioxol-4-yl)ethan-1-one shown in formula (V), comprising...

Claims

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Application Information

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IPC IPC(8): C07D317/54
CPCC07D317/54
Inventor 刘宝彪张浩
Owner 阜阳欣奕华制药科技有限公司
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