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Synthetic method of 2-(trimethylsilyl)phenyl trifluoromethane sulfonate

A technology of phenyl trifluoromethane sulfonate and trimethylsilyl is applied in the field of synthesis of pharmaceutical intermediates and chemical materials, and can solve the problems of difficult operation, harsh reaction conditions, and high cost of raw materials, and achieves reaction equipment. The effect of simple requirements, mild reaction conditions, and easy control of the reaction

Pending Publication Date: 2017-11-07
SHANGHAI JINGCHUN BIOCHEM TECH CO LTD
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Problems solved by technology

[0003] The synthesis and application of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate have been reported in many documents in recent years, but the reaction conditions are relatively harsh, it is difficult to control the reaction process, the process is complicated, and the operation is difficult. Difficulty, high cost of raw materials, not suitable for industrial production (Bronner SM1, Garg NK.J.Org.Chem.2009, 74, 8842; McAusland D1, Seo S, Pintori DG, Finlayson J, Greaney MF.Org Lett.2011 , 13, 3667)

Method used

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  • Synthetic method of 2-(trimethylsilyl)phenyl trifluoromethane sulfonate

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Embodiment

[0022] Process method for synthesizing 2-(trimethylsilyl) phenyl trifluoromethanesulfonate

[0023] The chemical equation of the synthesis process of the present invention is as follows:

[0024]

[0025] The specific implementation steps are:

[0026] 1. Synthesis of compound II

[0027]

[0028] (1) Prepare a 10L glass reactor. After the Ar replacement is complete, add 4L of toluene and 2-bromophenol (1.2kg, 6.94mol) in sequence, then heat to reflux at an internal temperature of about 100-110°C;

[0029] (2) Under reflux conditions, slowly add hexamethyldisilazane (HMDS) (1.23kg, 7.63mol) dropwise, with heat generation and alkaline gas generation;

[0030] (3) After the dripping is finished, continue to reflux and mature for 1 to 2 hours at an internal temperature of 105 to 115°C;

[0031] (4) Sampling and testing. After GC confirms that the raw material 2-bromophenol has disappeared, the temperature of the water bath is cooled down, the reaction liquid is cooled to below 40°C, and conc...

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Abstract

The invention discloses a synthetic method of 2-(trimethylsilyl)phenyl trifluoromethane sulfonate. The synthetic method is characterized by comprising the following steps: dropwise adding hexamethyl disilazane into 2-bromophenol, and carrying out maturing; dropwise adding n-butyllithium into reaction liquid, and carrying out maturing; dropwise adding pyridine into the reaction liquid; dropwise adding trifluoromethanesulfonic anhydride, and carrying out maturing; and purifying a reactant by virtue of a reduced pressure distillation, so as to obtain 2-(trimethylsilyl)phenyl trifluoromethane sulfonate. According to the synthetic method, GC purity of 2-(trimethylsilyl)phenyl trifluoromethane sulfonate can reach 98% or above, and the total yield is 60% or above.

Description

Technical field [0001] The invention relates to a method for synthesizing 2-(trimethylsilyl) phenyl trifluoromethanesulfonate, and belongs to the synthetic technical field of pharmaceutical intermediates and chemical material applications. Background technique [0002] The benzene ring structure of 2-(trimethylsilyl)phenyltrifluoromethanesulfonate contains highly reactive -OSO 2 CF 3 And -Si(CH 3 ) 3 The group has a very high application value in synthesis. It can be used to synthesize some biologically active benzopyran derivatives (H. Yoshida, Y. Ito, J. Ohshita, Chem. Commun. 2011, 47, 8512 ), it can be used to synthesize some new materials (TTJayanth, M. Jeganmohan, C.-H. Cheng, J. Organ. Chem. 2004, 69, 8445). Therefore, according to market demand, it is very necessary to study the synthesis process of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate to realize industrial production as soon as possible and reduce costs. [0003] Regarding the synthesis and application of 2-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08
CPCC07F7/081
Inventor 阚洪柱
Owner SHANGHAI JINGCHUN BIOCHEM TECH CO LTD
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