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A kind of preparation method of diaryl phosphorus chloride compound

A technology for diarylphosphorus chloride and compound, which is applied in the field of organic synthesis, can solve the problems of limited application, complicated synthesis of diarylphosphorus oxygen compounds, etc., and achieves the effects of less waste and mild reaction conditions

Active Publication Date: 2019-07-16
濮阳惠成新材料产业技术研究院有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The reaction needs to use hydrogen chloride gas, which limits its application in industrialization
Patent JPH0352894A reports a method for preparing diaryl phosphorus chloride compounds by reacting diaryl phosphorus oxide compounds with phosphorus trichloride, but the synthesis of diaryl phosphorus oxide compounds is relatively cumbersome

Method used

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  • A kind of preparation method of diaryl phosphorus chloride compound

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Embodiment 1 2

[0014] The synthesis of embodiment 1 diphenyl phosphorus chloride

[0015] Add triphenylphosphine (1mol, 262g), 1L carbon tetrachloride and zinc trifluoromethanesulfonate (0.01mol, 3.7g) into the dry reactor, and then add three Phosphorus chloride (0.5mol, 69g), after the dropwise addition, the temperature was raised to 60°C for 12 hours to stop the reaction. The reaction solution was filtered through diatomaceous earth, and the solvent was evaporated from the filtrate under normal pressure, and then diphenylphosphine chloride was distilled under reduced pressure to obtain 307g, with a yield of 93%; 31 P NMR (162MHz, CDCl 3 ),δ:80.5; 1 HNMR (400MHz, CDCl 3 ):7.65-7.68(m,4H),7.42-7.45(m,6H).

Embodiment 2 2

[0016] The synthesis of two (2-methylphenyl) phosphorus chlorides of embodiment 2

[0017] Add three (2-methylphenyl) phosphorus (1mol, 304g), 1L carbon tetrachloride and zinc trifluoromethanesulfonate (0.1mol, 36.2g) to the dry reactor, and then Phosphorus trichloride (0.5mol, 69g) was added dropwise to the system, and after the dropwise addition was completed, the temperature was raised to 80°C for 10 hours to stop the reaction. The reaction solution was filtered through diatomaceous earth, and the solvent was evaporated from the filtrate under normal pressure, and then distilled under reduced pressure to obtain 343 g of bis(2-methylphenyl)phosphorous chloride, with a yield of 92%; 31 P NMR (162MHz, CDCl 3 ):66.9; 1 HNMR (400MHz, CDCl 3 ):7.40-7.43(m,2H),7.21-7.25(m,2H),7.10-7.17(m,4H),2.41(s,6H).

Embodiment 3

[0018] The synthesis of two (4-methylphenyl) phosphorus chlorides of embodiment 3

[0019] Add three (4-methylphenyl) phosphorus (1.1mol, 334g), 1L carbon tetrachloride and zinc trifluoromethanesulfonate (0.05mol, 18.5g) to the dry reactor, and then Phosphorus trichloride (0.5mol, 69g) was added dropwise to the system, and after the dropwise addition was completed, the temperature was raised to 60°C for 12 hours to stop the reaction. The reaction solution was filtered through diatomaceous earth, and the solvent was evaporated from the filtrate under normal pressure, and then distilled under reduced pressure to obtain 339 g of bis(4-methylphenyl)phosphorous chloride, with a yield of 91%; 31 P NMR (162MHz, CDCl 3 ), δ: 81.6; 1 H NMR (400MHz, CDCl 3 ) 7.58 (d, J = 8.1 Hz, 4H), 7.34 (d, J = 8.1 Hz, 4H), 2.46 (s, 6H).

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Abstract

The invention discloses a method for preparing a diarylphosphochlorine compound and belongs to the field of organic synthesis. The method is as follows: the diarylphosphochlorine compound is preparedby reaction of triarylphosphine as a starting material with phosphorus trichloride in the presence of zinc trifluoromethanesulfonate as a catalyst and distillation. Compared with the prior art, the method has the advantages of high reaction yield and simple post-treatment, is particularly suitable for preparation of the diarylphosphochlorine compound with a substituent, and is more suitable for industrial production. The obtained diarylphosphochlorine compound can be used as a ligand for synthesizing metal catalysts, and is applied to the fields such as organic photoelectric materials and medicines.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and relates to a synthesis method of a class of organophosphorus compounds, in particular to a preparation method of diaryl phosphorus chloride compounds. Background technique [0002] Metal-catalyzed coupling reactions involving organophosphorus ligands are widely used in the synthesis of OLED functional materials, polymers, drug molecules, and bioactive compounds. The structure and properties of organophosphorus ligands provide a good basis for adjusting the performance of transition metal complex catalysts and realizing the synthesis of diverse catalysts that meet the needs of various reactions. In the design and synthesis of phosphorus ligands, aryl phosphorus chloride compounds, as important organic intermediates, play a crucial role in the diversity of phosphorus ligand structures. [0003] At present, the preparation method of diphenyl phosphorus chloride compound is usually by benzene an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/52
CPCC07F9/52
Inventor 陈辉杨振强周铎杨瑞娜张垚张银龙孙敏青张海朗
Owner 濮阳惠成新材料产业技术研究院有限公司
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