Synthesis method of 2-bromo-2-(2-fluoro-3-methoxyphenyl)ethyl acetate

A technology of methoxyphenyl and ethyl acetate, which is applied in the synthesis field of synthetic methods, can solve the problems of lengthy reaction route and low total reaction yield, and achieve low reaction energy consumption, low total yield and short preparation cycle Effect

Inactive Publication Date: 2019-05-03
安徽华胜医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In the technical scheme reported in this patent document, 1-fluoro-2-methoxybenzene (II) is used as the starting material to synthesize the compound in four steps, and the reaction route is lengthy, resulting in low overall reaction yield

Method used

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  • Synthesis method of 2-bromo-2-(2-fluoro-3-methoxyphenyl)ethyl acetate
  • Synthesis method of 2-bromo-2-(2-fluoro-3-methoxyphenyl)ethyl acetate
  • Synthesis method of 2-bromo-2-(2-fluoro-3-methoxyphenyl)ethyl acetate

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Experimental program
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Effect test

Embodiment 1

[0036] A kind of synthetic method of 2-bromo-2-(2-fluoro-3-methoxyphenyl) ethyl acetate, synthetic route is as follows:

[0037]

[0038] The synthetic method of above-mentioned 2-bromo-2-(2-fluoro-3-methoxyphenyl) ethyl acetate comprises the following steps:

[0039] One, the preparation of formula VI compound:

[0040] (1) 1.0 g, 1 equiv. of the compound of formula II was dissolved in 5 mL of diethyl ether in a constant pressure dropping funnel to prepare a diethyl ether solution of the compound of formula II for subsequent use;

[0041] Based on the compound of formula II, 1 equiv. of ethyl chloroacetate was dissolved in 3 mL of diethyl ether in a constant pressure dropping funnel to prepare a diethyl ether solution of ethyl chloroacetate for subsequent use;

[0042] (2) In terms of the compound of formula II, add 1.2 equiv. of n-butyllithium ether solution into the reactor, after cooling to -78°C, add 1.2 equiv. of TMEDA, stir and disperse, and add the The ether solut...

Embodiment 2

[0047] A kind of synthetic method of 2-bromo-2-(2-fluoro-3-methoxyphenyl) ethyl acetate, synthetic route is as follows:

[0048]

[0049] The synthetic method of above-mentioned 2-bromo-2-(2-fluoro-3-methoxyphenyl) ethyl acetate comprises the following steps:

[0050] One, the preparation of formula VI compound:

[0051] (1) 0.5 g, 1 equiv. of the compound of formula II was dissolved in 2.5 mL of diethyl ether in a constant pressure dropping funnel to prepare a diethyl ether solution of the compound of formula II for subsequent use;

[0052] Based on the compound of formula II, 1.1 equiv. of ethyl chloroacetate was dissolved in 1 mL of diethyl ether in a constant pressure dropping funnel to prepare a diethyl ether solution of ethyl chloroacetate for subsequent use;

[0053](2) In terms of the compound of formula II, add 1.1 equiv. of n-butyllithium ether solution into the reactor, cool to -85°C, add 1.1 equiv. of TMEDA, stir and disperse, and add The ether solution of Com...

Embodiment 3

[0058] A kind of synthetic method of 2-bromo-2-(2-fluoro-3-methoxyphenyl) ethyl acetate, synthetic route is as follows:

[0059]

[0060] The synthetic method of above-mentioned 2-bromo-2-(2-fluoro-3-methoxyphenyl) ethyl acetate comprises the following steps:

[0061] One, the preparation of formula VI compound:

[0062] (1) Dissolve 1.5 g, 1 equiv. of the compound of formula II in 15 mL of diethyl ether in a constant pressure dropping funnel to prepare a diethyl ether solution of the compound of formula II for subsequent use;

[0063] Based on the compound of formula II, 1.4 equiv. of ethyl chloroacetate was dissolved in 3 mL of ether in a constant pressure dropping funnel to prepare an ether solution of ethyl chloroacetate for subsequent use;

[0064] (2) Based on the compound of formula II, add 1.4 equiv. of n-butyllithium ether solution into the reactor, cool to -75°C, add 1.4 equiv. of TMEDA, stir and disperse, and add The ether solution of Compound II was added drop...

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Abstract

The invention discloses a synthesis method of 2-bromo-2-(2-fluoro-3-methoxyphenyl)ethyl acetate. The synthesis route is as shown as the follows. The synthesis method comprises the following two stepsof synthesizing a compound represented by a formula I and synthesizing a compound represented by a formula VI. The target compound is prepared by adopting a two-step method according to the synthesisscheme disclosed by the invention, reaction energy consumption is low, "three wastes (waste gas, waste water and industrial residue)" are few, the preparation period is short, and impurity productioncapacity is low.

Description

technical field [0001] The invention relates to the technical field of mechanical synthesis and pharmaceutical intermediates, in particular to a synthesis method of ethyl 2-bromo-2-(2-fluoro-3-methoxyphenyl)acetate. Background technique [0002] Eagolix has been approved by the FDA for the treatment of pain caused by endometriosis and is the first oral drug for this indication in more than a decade. [0003] Based on the good therapeutic effect of eagolix, the market has a great demand for elagolix raw materials and intermediates. The structure of elagolix is ​​as follows: [0004] [0005] 2-Bromo-2-(2-fluoro-3-methoxyphenyl) ethyl acetate is used as a key intermediate in the synthesis of elagolix, and its structure is shown in formula I: [0006] [0007] The patent number is: WO2009062087, which discloses the synthesis method of this compound. The reaction process is as follows: [0008] [0009] In the technical scheme reported in this patent document, the com...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/307C07C69/734
Inventor 胡志刚许良志何大荣杜小鹏钱祝进何勇
Owner 安徽华胜医药科技有限公司
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