Synthesis method of aromatic vinyl trifluoromethylthio ether compound
A technique for the synthesis of aromatic vinyl trifluoromethyl sulfide, which is applied in the fields of sulfide preparation, organic chemistry, etc., can solve the problems of low substrate universality, long reaction time, high reaction temperature, etc., and achieve good industrial application Foreground, high substrate universality, good catalytic effect
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[0027] Example 1: Synthesis of trans-4-methylstyryl trifluoromethyl sulfide
[0028] Weigh out 0.082g of trans-4-methylnitrostyrene, 0.125g of silver trifluoromethyl sulfide, 0.014g of copper trifluoroacetate, 0.174g of dipotassium hydrogen phosphate and 0.228g of ammonium persulfate, and add the magnetic stirrer in turn. Add 5.0 mL of dimethyl sulfoxide to the 50 mL reaction tube of the tube, and place it in a nitrogen atmosphere at 60°C for 4-6 hours.
[0029] After the reaction, the reaction solution was filtered, washed, dried, and separated and purified sequentially to obtain 0.093 g of a colorless oily liquid with a yield of 85%. 1 H NMR(400MHz, CDCl 3 )δ7.32(d,J=8.1Hz,2H), 7.20(d,J=8.0Hz,2H), 7.02(d,J=15.3Hz,1H), 6.70(d,J=15.3Hz,1H) ,2.39(s,4H); 19 F NMR(376MHz, CDCl 3 )δ-42.91(s,3F); 13 C NMR(101MHz, CDCl 3 )δ141.76(d,J=0.7Hz),139.4(s),132.4(s),129.7(q,J=307.9Hz),129.6(s),126.8(s),110.3(q,J=3.0 Hz), 21.3(s).
Example Embodiment
[0030] Example 2: Synthesis of trans-4-tert-butyl styryl trifluoromethyl sulfide
[0031] Weigh out 0.103g of trans-4-tert-butylnitrostyrene, 0.125g of silver trifluoromethyl sulfide, 0.014g of copper trifluoroacetate, 0.174g of dipotassium hydrogen phosphate and 0.228g of ammonium persulfate, and add them in sequence with magnetic stirring Add 5.0 mL of dimethyl sulfoxide to the 50 mL reaction tube of the submerged, and place it in a nitrogen atmosphere at 60°C for 4-6 hours.
[0032] After the reaction, the reaction solution was filtered, washed, dried, and separated and purified sequentially to obtain 0.107 g of a colorless oily liquid with a yield of 82%. 1 H NMR(400MHz, CDCl 3 )δ7.45(d,J=8.5Hz,2H), 7.40(d,J=8.5Hz,2H), 7.06(d,J=15.3Hz,1H), 6.75(d,J=15.2Hz,1H) ,1.38(s,9H); 19 F NMR(376MHz, CDCl 3 )δ-42.91(s,3F); 13 C NMR(101MHz, CDCl 3 )δ152.7(s),141.8(d,J=0.8Hz),132.4(s),129.7(q,J=307.9Hz),126.7(s),125.8(s),110.5(q,J=3.0 Hz), 34.8(s), 31.2(s).
Example Embodiment
[0033] Example 3: Synthesis of trans-4-chlorostyryl trifluoromethyl sulfide
[0034] Weigh out 0.092g of trans-4-chloronitrostyrene, 0.125g of silver trifluoromethyl sulfide, 0.014g of copper trifluoroacetate, 0.174g of dipotassium hydrogen phosphate and 0.228g of ammonium persulfate, and add them in sequence with a magnetic stirrer. Add 5.0 mL of dimethyl sulfoxide to a 50 mL reaction tube, and place it in a nitrogen atmosphere at 60°C for 4-8 hours.
[0035] After the reaction, the reaction solution was filtered, washed, dried, separated and purified in sequence to obtain 0.086 g of a colorless oily liquid with a yield of 72%. 1 H NMR(400MHz, CDCl 3 )δ7.35(s,4H), 6.97(d,J=15.4Hz,1H), 6.75(d,J=15.4Hz,1H); 19 F NMR(376MHz, CDCl 3 )δ-42.62(s,3F); 13 C NMR(101MHz, CDCl 3 )δ139.3(d,J=0.7Hz),135.0(s),133.6(s),129.6(q,J=308.0Hz),129.1(s),127.97(s),112.7(dd,J=6.3 ,3.1Hz). Comparative example 1:
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