A kind of diaryl phosphorus compound with hydroxyphenyl functional group and preparation method thereof
A technology of hydroxyphenyl functional and phosphorus compounds, which is applied in the field of diaryl phosphorus compounds and their preparation, can solve the problems of narrow substrate range and limited application, and achieve wide substrate range, excellent yield, and good chemoselectivity Effect
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Embodiment 1
[0033] A sulfonylalkyl-substituted phenolic compound (0.5 mmol) was dissolved in 5 mL of toluene, and 0.5 mmol of diphenylphosphine was added to the system. Potassium carbonate (0.5 mmol) was then added to the reaction mixture, and the reaction was stirred at 30°C for 12 hours. After completion of the reaction, add water to quench; leave to separate the liquids, extract the aqueous layer 4 times with dichloromethane, combine the organic phases, dry over anhydrous sodium sulfate, filter, remove the solvent under reduced pressure and obtain the organophosphorus compound (180.8mg, Productive rate 80%), its structural formula is figure 1 Be the proton nuclear magnetic resonance spectrum of product in embodiment 1, by figure 1 According to the chemical shift value and integral ratio of the proton nuclear magnetic resonance spectrum, it can be inferred that it is the structure shown in the above structural formula. Combined with 13C NMR, 31P NMR, 19F NMR and high-resolution mass...
Embodiment 2
[0036]A sulfonylalkyl-substituted phenolic compound (0.5 mmol) was dissolved in 5 mL of tetrahydrofuran, and 0.4 mmol of diphenylphosphine was added to the system. Potassium carbonate (0.4 mmol) was then added to the reaction mixture, and the reaction was stirred at 60° C. for 1 hour. After completion of the reaction, add water to quench; leave to separate the liquids, extract the aqueous layer 8 times with dichloromethane, combine the organic phases, dry over anhydrous sodium sulfate, filter, remove the solvent under reduced pressure and obtain the organophosphorus compound (186.4mg, Productive rate 87%), its structural formula is figure 2 Be the proton nuclear magnetic resonance spectrum of product in embodiment 2, as shown in the figure, figure 2 According to the chemical shift value and integral ratio of the proton nuclear magnetic resonance spectrum, it can be inferred that it is the structure shown in the above structural formula. Combined with 13C NMR, 31P NMR and...
Embodiment 3
[0039] A sulfonylalkyl-substituted phenolic compound (0.5 mmol) was dissolved in 5 mL of ethyl acetate, and 1 mmol of diphenylphosphine was added to the system. Cesium carbonate (1 mmol) was then added to the reaction mixture, and the reaction was stirred at 90°C for 12 hours. After completion of the reaction, add water to quench; leave to separate the liquids, extract the aqueous layer 6 times with dichloromethane, combine the organic phases, dry over anhydrous sodium sulfate, filter, and remove the solvent under reduced pressure by column chromatography to obtain an organophosphorus compound (135.4 mg, Yield 84%). Its structural formula is The specific structural identification data are:
[0040] (1-(2-Hydroxyphenyl)ethyl)diphenylphosphine oxide:1H NMR(400MHz,CDCl3)δ10.20(s,1H),7.94–7.80(m,2H), 7.70–7.48(m,5H),7.47–7.28 (m,3H),7.13–7.04(m,1H), 6.96–6.93(m,1H),6.84–6.81(m,1H),6.67(t,J=7.4Hz, 1H),3.64(dt,J =9.4,7.4Hz,1H), 1.59(dd,J=15.9,7.5 Hz,3H); 13C NMR(100MHz,CDCl3)δ1...
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