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A kind of preparation method of diaryl phosphorus bromide compound

A technology of diarylphosphorus bromide compound and triarylphosphorus, which is applied in the field of organic synthesis, can solve the problems of limited application, complicated synthesis of diarylphosphorus oxycompound and the like, and achieves the effects of simple steps and mild reaction conditions

Active Publication Date: 2019-07-16
PUYANG HUICHENG ELECTRONICS MATERIAL
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

The reaction requires the use of hydrogen bromide gas, which has higher requirements on equipment, which limits its application in industrialization
Patent JPH0352894A reports a method for preparing diaryl phosphorus bromide compounds by reacting diaryl phosphorus oxides with phosphorus tribromide, but the synthesis of diaryl phosphorus oxides is tedious

Method used

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  • A kind of preparation method of diaryl phosphorus bromide compound

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Embodiment 1

[0014] The synthesis of embodiment 1 diphenylphosphorus bromide

[0015] Add triphenylphosphine (1mol, 262g), 1L carbon tetrachloride and iron bromide (0.01mol, 2.93g) to the dry reactor, then add phosphorus tribromide dropwise to the system at 0-10°C (0.5mol, 134g), after the dropwise addition, the temperature was raised to 60°C for 12 hours, and the reaction was stopped. The reaction solution was filtered through diatomaceous earth, and the filtrate was evaporated to remove the solvent under normal pressure, and then diphenylphosphonium bromide was distilled under reduced pressure to obtain 361 g, with a yield of 92%; 31 P NMR (162MHz, CDCl 3 ):72.8; 1 HNMR (400MHz, CDCl 3 ):7.67(m,4H),7.43(m,6H); 13 CNMR (100MHz, CDCl 3 ): 137.3 (d, J = 36Hz), 132.7 (d, J = 24Hz), 130 (s), 128.6 (d, J = 6.5Hz).

Embodiment 2

[0016] Example 2 Synthesis of two (4-methylphenyl) phosphorus bromide

[0017] Add three (4-methylphenyl) phosphorus (1.1mol, 334g), 1L carbon tetrachloride and ferric bromide (0.1mol, 29.2g) to the dry reactor, and then add the system under the condition of 0-10℃ Phosphorus tribromide (0.5mol, 134g) was added dropwise to the mixture, and after the addition was completed, the temperature was raised to 70°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 407 g of bis(4-methylphenyl)phosphorus bromide, with a yield of 93%; 31 P NMR (162MHz, CDCl 3 ):75.0; 1 H NMR (400MHz, CDCl 3 ):7.57(d, J=8.0Hz, 4H), 7.32(d, J=8.0Hz, 4H), 2.47(s, 6H); 13 C NMR (100MHz, CDCl 3 ): 140.8(s), 132.2(d, J=57Hz), 132.8(d, J=39Hz), 129.6(m), 21.5(s).

Embodiment 3

[0018] Example 3 Synthesis of two (4-trifluoromethylphenyl) phosphorus bromide

[0019] Three (4-trifluoromethylphenyl) phosphorus (1mol, 466g), 1L carbon tetrachloride and ferric bromide (0.05mol, 14.6g) were added to the dry reactor, and then heated at 0-10°C Phosphorus tribromide (0.5mol, 134g) was added dropwise into the system, and after the dropwise addition, 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 546 g of bis(4-trifluoromethylphenyl)phosphorus bromide, with a yield of 91%; 31 P NMR (162MHz, CDCl 3 ):64.3; 1 HNMR (400MHz, CDCl 3 ):7.75(t, J=7.5Hz, 4H), 7.69(d, J=7.5Hz, 4H); 13 C NMR (100MHz, CDCl 3 ):141.0(d, J=39Hz), 133.0(d, J=24Hz), 131.6(d, J=12Hz), 125.6(m), 123.6(q, J=272Hz, CF 3 ).

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Abstract

The invention discloses a preparation method of a diaryl phosphorus-bromine compound, belonging to the field of organic synthesis. By taking triaryl phosphorus as an initial raw material and iron bromide as a catalyst, the diaryl phosphorus-bromine compound is obtained by carrying out a reaction with phosphorus tribromide and carrying out distillation. Compared with the prior art, the preparationmethod is high in reaction yield, simple in post-treatment and more suitable for industrial production. The prepared diaryl phosphorus-bromine compound can be used for synthesizing a ligand of a metalcatalyst and is applied to the fields of organic photoelectric materials and medicines and the like.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and relates to a synthesis method of a class of organic phosphorus compounds, in particular to a preparation method of a diaryl phosphorus bromide compound. 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. In terms of the design and synthesis of phosphorus ligands, diaryl phosphorus bromide compounds are important organic intermediates, which have higher activity than diaryl phosphorus chloride compounds (Chem.Eur.J.2011,17,10828-10831 ), so when it is applied to the synthesis of organophosphorus ligands, the yield of the product is higher. In terms of the diversity of phosphorus ligands, aryl phosphorus bromide compounds also have incomparable advantages. [0003] At present, the preparation method of diphenylphosphorus bromide com...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/52
CPCC07F9/52
Inventor 张银龙陈辉赵顺伟杨振强屈凤波周铎杨瑞娜
Owner PUYANG HUICHENG ELECTRONICS MATERIAL
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