3-sulfonic group-4-halophenyl-3'-sulfophenyl-4''-halophenylphosphine oxide and preparation method of salt thereof
A technology of sulfophenyl and halophenyl phosphine oxide, which is applied in chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, organic chemistry, etc., can solve problems that are not economical and large-scale production. Feasibility and other issues, to achieve the effect of shortening the preparation cycle, reducing the dosage, and simplifying the post-processing process
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Embodiment 1
[0040] At room temperature and in a nitrogen atmosphere, bis(4-fluorophenyl)phenylphosphine oxide (12.9g, 41.1mmol) and oleum (30ml, 144mmol) with a concentration of 20% were dropped into a 100ml three-necked flask successively, and placed Stir the reaction in an oil bath at 120°C, monitor by TLC until the reaction is complete, pour the reaction system into 300ml of ice water after it naturally drops to room temperature, adjust the pH to neutral with NaOH aqueous solution, add 200mL of N,N-dimethylacetamide and Toluene (volume ratio 2:1), reflux for water separation, suction filtration, the filtrate was evaporated to remove the solvent under reduced pressure, and the obtained solid was recrystallized three times with water and isopropanol (volume ratio 1:18) to obtain 3-sodium sulfonate-4- 5.84 g of fluorophenyl-3'-sodium sulfonate phenyl-4''-fluorophenylphosphine oxide (27% yield). 1 HNMR(400 MHz, DMSO-d6), δ: 7.96~8.01(m, 1H), 7.90~7.93(d, J = 12.0Hz, 1H), 7.84~7.86(d, J =...
Embodiment 2
[0043]Bis(4-chlorophenyl)phenylphosphine oxide (14.27g, 41.10mmol) was reacted with oleum (20%, 30ml) at 120°C for 24 hours. Pour the reaction system into 300ml of ice water after the reaction system has naturally dropped to room temperature, adjust the pH to neutral with NaOH aqueous solution, add 200ml of N,N-dimethylacetamide and toluene (volume ratio 2:1), reflux to separate water, suction filter, and the filtrate The solvent was evaporated under reduced pressure, and the obtained solid was recrystallized three times with water and isopropanol (volume ratio 1:16) to obtain 3-sodium sulfonate-4-chlorophenyl-3'-sodium sulfonate phenyl-4''- Chlorophenylphosphine oxide 6.57g, yield 29%. 1 HNMR(400 MHz, DMSO-d6), δ: 7.98~8.03(m, 1H), 7.92~7.95(d, J = 12.0Hz, 1H), 7.86~7.88(d, J = 7.6Hz, 1H), 7.66~7.72(m, 2H), 7.51~7.59(m, 3H), 7.41~7.47(m, 2H), 7.35~7,38(t, J = 9.8Hz, 1H); 31 PNMR(162 MHz, DMSO-d6), δ: 24.69(s, P); 13 CNMR (100 MHz, DMSO-D6), Δ: 116.33, 117.13, 127.06, 12...
Embodiment 3
[0046] Bis(4-fluorophenyl)phenylphosphine oxide (12.92g, 41,10mmol) and oleum (20%, 30ml) were reacted at 120°C for 24 hours. Pour the reaction solution into ice water after cooling, adjust the pH to neutral with KOH, add 200ml N,N-dimethylacetamide and toluene (volume ratio 2:1), reflux to separate water, filter with suction, evaporate the filtrate to remove the solvent under reduced pressure , the resulting solid was recrystallized three times with water and isopropanol (volume ratio 1:12) to obtain the target product 3-sulfonate potassium-4-fluorophenyl-3'-sulfonate potassium phenyl-4''-fluorophenyl Phosphine oxide 6.79g, yield 30%. 1 HNMR(400 MHz, DMSO-d6), δ: 7.99~8.05(m, 1H), 7.93~7.96(d, J = 12.0Hz, 1H), 7.87~7.89(d, J = 7.6Hz, 1H), 7.67~7.73(m, 2H), 7.52~7.60(m, 3H), 7.44~7.50(m, 2H), 7.37~7,41(t, J = 9.8Hz, 1H); 31 PNMR(162 MHz, DMSO-d6), δ: 24.70(s, P); 13 CNMR(100 MHz, DMSO-d6), δ: 116.34, 117.14, 127.07, 128.52, 129.47, 131.34, 13171, 132.41, 134.36, 134.77, 1...
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