A kind of preparation method of o-alkylphenyl phosphonothioate
A technology of alkyl phenyl thiophosphonate and alkyl phenyl phosphonite, which is applied in the field of preparation of O-alkyl phenyl thiophosphonate, can solve the problems of long reaction time and the like, and achieves operation Convenience, wide substrate range, simple process effect
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[0024] A kind of preparation method of O-alkylphenyl phosphonothioate of the present invention comprises the following steps:
[0025] (1) Add sulfonyl chloride and alkyl phenylphosphonite to the organic solvent, then add copper salt catalyst and L-proline ligand or bipyridine ligand, and react at 50-100°C for 2-10 hours ;
[0026] (2) After the reaction is finished, the reaction solution is concentrated, and O-alkylphenylphosphonothioate is obtained after separation and purification.
[0027] General reaction formula of the present invention is as follows:
[0028]
[0029] Among them, R 1 is one or more of methyl, ethyl, isopropyl or n-propyl; R 2 It is naphthyl, unsubstituted or substituted phenyl, thiophene and other heterocycles, and alkyl, and the substituent is one of alkoxy, alkyl, halogen or trifluoromethyl.
Embodiment 1
[0031] The preparation method of O-ethyl-S-(4-methylphenyl) phenylphosphonothioate comprises the following steps:
[0032] Weigh 2.0 mmol of ethyl phenylphosphonite and 0.5 mmol of p-toluenesulfonyl chloride in a reaction flask, add 5% copper chloride dihydrate as a catalyst, and 10% of L-proline as a ligand, Add 1.0 mL of tetrahydrofuran and react at 80°C for 3 h. After the reaction, the reaction solution is concentrated under reduced pressure and separated by column chromatography using ethyl acetate / petroleum ether=1:5 (v / v) as the developing solvent to obtain 130 mg of the target compound.
[0033] The target product yield of this embodiment 1 is 89%.
[0034] Such as figure 1 As shown, the NMR characterization of the target product is carried out as follows: 1 H NMR (500MHz, CDCl 3 -d)δ7.68–7.64(m,2H),7.50–7.47(m,1H),7.38–7.34(m,2H),7.17–7.15(m,2H),7.02–7.00(m,2H), 4.38–4.29(m,2H),2.28(s,3H),1.39(t,J=7.1Hz,1H).
Embodiment 2
[0036] The preparation method of O-ethyl-S-(4-methoxyphenyl) phenylphosphonothioate comprises the following steps:
[0037] Weigh 2.0mmol of ethyl phenylphosphonite and 0.5mmol of p-methoxybenzenesulfonyl chloride in a reaction flask, add 5% copper chloride dihydrate as a catalyst, and 10% of L-proline as a ligand , add 1.0mL tetrahydrofuran, and react at 80°C for 3h. After the reaction, the reaction solution is concentrated under reduced pressure, and separated by column chromatography using ethyl acetate / petroleum ether=1:3(v / v) as the developing solvent to obtain 133mg of the target compound .
[0038] The target product yield of this embodiment 2 is 86%.
[0039] Such as figure 2 As shown, the NMR characterization of the target product is carried out as follows: 1 H NMR (500MHz, CDCl 3 -d)δ7.66–7.62(m,2H),7.50–7.47(m,1H),7.38–7.34(m,2H),7.18–7.16(m,2H),6.74–6.72(m,2H), 4.39–4.27(m,2H),3.74(s,3H),1.39(t,J=7.0Hz,3H).
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