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Preparation method of 2-methoxy-5-fluorobromoacetophenone

A fluorobromoacetophenone, methoxyl technology, applied in the field of preparation of 2-methoxy-5-fluorobromoacetophenone, can solve the problems of high cost, large pollution, low yield and the like, and achieves Low price, little pollution, easy to deal with

Active Publication Date: 2021-09-07
无锡双启科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In the above synthesis method, in the process of synthesizing 2-methoxy-5-fluorobromoacetophenone compound I, the second step reaction uses cuprous bromide or bromine on bromine, not only the yield is low, but also the pollution is large, High cost, not conducive to industrial scale-up

Method used

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  • Preparation method of 2-methoxy-5-fluorobromoacetophenone

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Embodiment 1

[0023] A kind of preparation method of 2-methoxy group-5-fluorobromoacetophenone, described preparation method comprises the steps:

[0024] Add 126g (1mol) p-fluoroanisole, 1000ml carbon disulfide, 146.3g (1.1mol) aluminum trichloride to the reaction flask, then add 222g (1.1mol) bromoacetyl bromide, and stir at 20°C for 12 hours after adding, HPLC Track the reaction until the reaction of p-fluoroanisole is complete; quench into 2000ml of ice water, adjust the pH=2, add 1000ml of dichloromethane to extract the layers, concentrate the organic layer to dryness, and recrystallize from n-hexane to obtain 192g of 2-methoxy -5-fluorobromoacetophenone, molar yield: 78%.

[0025] figure 1 It is the hydrogen spectrum of 2-methoxy-5-fluorobromoacetophenone, 1 H-NMR (400MHz, CDCl 3 )δ: 7.56~7.53(dd, 1H, Ph-H), 7.23~7.21(d, 1H, Ph-H), 6.97~6.94(dd, 1H, Ph-H), 4.59(s, 2H, CH 2 ), 3.94 (s, 3H, OCH 3 ).

[0026] figure 2 It is a gas chromatogram of 2-methoxy-5-fluorobromoacetophenon...

Embodiment 2

[0028] A kind of preparation method of 2-methoxy group-5-fluorobromoacetophenone, described preparation method comprises the steps:

[0029] Add 126g (1mol) p-fluoroanisole, 1000ml carbon tetrachloride, 199.5g (1.5mol) aluminum trichloride to the reaction flask, then add 302.7g (1.5mol) bromoacetyl bromide, and stir at 40°C after adding After 2 hours, HPLC followed the reaction until the reaction of p-fluoroanisole was complete; quenched into 2000ml of ice water, adjusted to pH=2, added 1000ml of dichloromethane for extraction and separation, concentrated the organic layer to dryness, and recrystallized with n-hexane to obtain 177.8g 2-methoxy-5-fluorobromoacetophenone, molar yield: 72%.

Embodiment 3

[0031] A kind of preparation method of 2-methoxy group-5-fluorobromoacetophenone, described preparation method comprises the steps:

[0032] Add 126g (1mol) p-fluoroanisole, 1000ml dichloromethane, 195g (1.3mol) trifluoromethanesulfonic acid to the reaction flask, add 262.3g (1.3mol) bromoacetyl bromide in batches, and stir at 30°C after adding After 6 hours, HPLC followed the reaction until the reaction of p-fluoroanisole was complete; quenched into 2000ml of ice water, separated into layers, concentrated the organic layer to dryness, and recrystallized with n-hexane to obtain 167.3g of 2-methoxy-5-fluorobromide Substituted acetophenone, molar yield: 68%.

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Abstract

The invention discloses a preparation method of 2-methoxy-5-fluorobromoacetophenone. The method comprises the following steps: taking p-fluoroanisole as an initial raw material, and reacting with bromoacetyl bromide under the condition of Lewis acid to generate a compound I, namely 2-methoxy-5-fluorobromoacetophenone. In the one-step synthesis route process taking the p-fluoroanisole as the initial raw material, a large amount of reagents with high toxicity and high pollution are avoided, and meanwhile, the raw materials are low in price, so that the whole synthesis process is low in pollution and easy to treat.

Description

technical field [0001] The invention relates to the technical field of synthesis of pharmaceutical intermediates, in particular to a preparation method of 2-methoxy-5-fluorobromoacetophenone. Background technique [0002] 2-Methoxy-5-fluorobromoacetophenone is a key intermediate. WO2019 / 63748, Bioorganic and Medicinal Chemistry Letters, 2007, vol.17, #5, p.1291-1295 disclose the following synthesis of 2- The route of methoxy-5-fluorobromoacetophenone compound I: [0003] [0004] In the above synthesis method, in the process of synthesizing 2-methoxy-5-fluorobromoacetophenone compound I, the second step reaction uses cuprous bromide or bromine on bromine, not only the yield is low, but also the pollution is large, The cost is high, which is not conducive to industrial scale-up. Contents of the invention [0005] Aiming at the above-mentioned problems in the prior art, the present invention provides a preparation method of 2-methoxy-5-fluorobromoacetophenone. The prep...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/46C07C49/84
CPCC07C45/46C07C49/84Y02P20/55
Inventor 张国强王昌军秦英
Owner 无锡双启科技有限公司
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