A kind of preparation method of [(1,2-disulfonyl) ethyl] arene compound
A bissulfonyl compound technology, which is applied in the field of preparation of [ethyl] aromatic hydrocarbon compounds, can solve the problems of large substitution restriction of substrate functional groups, failure to realize bissulfonylation reaction, etc., and achieves good substrate compatibility, The effect of low cost and good application prospect
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Embodiment 1
[0022]
[0023] Add K to the reaction tube sequentially 2 S 2 o 5 (3.0 equiv) and Na 2 HPO 4 (2.0 equivalents), replace the air in the test tube with high-purity nitrogen and add 2 mL of DMF as a solvent. Then p-fluorostyrene (0.2 mmol), 1-iodobutane (4.0 equivalents) and triisopropylsilane (2.0 equivalents) were sequentially added with a microsampler, and stirred at 50° C. for 24 hours. After the reaction, the reaction solution was diluted with EA, extracted with water and saturated brine respectively, then the organic layer was dried, concentrated and separated by column chromatography to obtain the corresponding 1,2-bissulfone-substituted compound 3a in 57% yield.
[0024] 1 H NMR (400MHz, CDCl 3 ) δ (ppm) 7.56 (dd, J = 8.4, 5.2Hz, 2H), 7.17 (t, J = 8.4Hz, 2H), 4.74 (dd, J = 10.7, 2.1Hz, 1H), 3.95 (dd, J =14.4, 1.9Hz, 1H), 3.69(dd, J=14.3, 10.9Hz, 1H), 2.89-2.58(m, 4H), 1.79-1.68(m, 4H), 1.43-1.27(m, 4H), 0.91-0.85 (m, 6H); 19 F NMR (376MHz, CDCl 3 ) δ-109.9--1...
Embodiment 2
[0026]
[0027] Add K to the reaction tube sequentially 2 S 2 o 5 (3.0 equiv) and Na 2 HPO 4 (2.0 equivalents), replace the air in the test tube with high-purity nitrogen and add 2 mL of DMF as a solvent. Then, 2-vinylthiophene (0.2 mmol), 1-iodobutane (4.0 equivalents) and triisopropylsilane (2.0 equivalents) were sequentially added with a micro injector, and stirred at 50° C. for 24 hours. After the reaction, the reaction solution was diluted with EA, extracted with water and saturated brine respectively, then the organic layer was dried, concentrated and separated by column chromatography to obtain the corresponding 1,2-bissulfone group-substituted compound 3b in a 70% yield.
[0028] 1 H NMR (400MHz, CDCl 3 ) δ (ppm) 7.48 (d, J = 5.0Hz, 1H), 7.32 (d, J = 3.3Hz, 1H), 7.10 (dd, J = 4.9, 3.8Hz, 1H), 5.00 (dd, J = 10.9 , 2.3Hz, 1H), 3.92(dd, J=14.6, 2.2Hz, 1H), 3.67(dd, J=14.5, 11.0Hz, 1H), 2.98-2.68(m, 2H), 2.63-2.48(m, 2H), 1.85-1.60(m, 4H), 1.44-1.20(m, 4H), 0.91...
Embodiment 3
[0030]
[0031] Add K to the reaction tube sequentially 2 S 2 o 5 (3.0 eq), Na 2 HPO 4 (2.0 equivalents) and p-phenylstyrene (0.2 mmol), after replacing the air in the test tube with high-purity nitrogen, 2 mL of DMF was added as a solvent. Then ethyl 4-iodobutyrate (4.0 eq) and triisopropylsilane (2.0 eq) were sequentially added using a micro injector, and stirred at 50° C. for 24 hours. After the reaction, the reaction solution was diluted with EA, extracted with water and saturated brine respectively, then the organic layer was dried, concentrated and separated by column chromatography to obtain the corresponding 1,2-bissulfone group-substituted compound 3c in 58% yield.
[0032] 1 HNMR (400MHz, CDCl 3 ) δ (ppm) 7.72-7.61 (m, 6H), 7.48 (t, J = 7.5Hz, 2H), 7.40 (t, J = 7.2Hz, 1H), 4.80 (d, J = 10.4Hz, 1H), 4.16-3.98(m, 5H), 3.81(dd, J=14.4, 10.9Hz, 1H), 3.08-2.73(m, 4H), 2.54-2.31(m, 4H), 2.18-1.97(m, 4H), 1.22(t, J=7.1Hz, 6H); 13 C NMR (100MHz, CDCl 3 )δ (ppm) ...
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