A kind of synthetic method of 2-phenyl-3-methylbenzofuran compound
A synthesis method and technology of methylbenzene, applied in the direction of organic chemistry, etc., can solve problems such as expensive catalysts and serious environmental pollution, and achieve the effects of wide application range, high reaction yield, and simple and convenient reaction operation
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Embodiment 1
[0030] Substrate 1 (1 mmol) was dissolved in mesitylene (2 mL), the reaction mixture was heated to 180 ° C, and stirred for 4 hours. After the reaction was completed, the target product a was separated by flash column chromatography with a yield of 35 %. Its reaction equation is:
[0031]
[0032] The spectral data of product a is: 1 H NMR (600MHz, CDCl 3 )δ7.46(d, J=7.4Hz, 2H), 7.42(d, J=7.1Hz, 2H), 7.39(t, J=8.4Hz, 5H), 7.33(m, 2H), 7.25(m, 5H), 7.08(d, J=2.2Hz, 1H), 6.97(dd, J=8.5, 2.2Hz, 1H), 6.32(d, J=2.2Hz, 1H), 6.29(d, J=2.2Hz, 1H), 5.93(s,1H), 5.12(s,2H), 5.04(s,2H), 5.02(s,2H), 2.09(s,3H); 13 C NMR (150MHz, CDCl 3 )δ161.7,158.6,157.3,156.7,155.6,143.9,137.1,136.8,136.7,128.8,128.7,128.6,128.3,128.1,127.8,127.7,127.6,127.1,124.1,119.7,115.8,112.2,100.4,97.3,94.7 ,94.2,70.8,70.6,70.30,9.26; HRMS(ESI):m / z:Calcd.for C 36 h 30 o 5 [M+H] + 543.2166, Found 543.2173.
Embodiment 2
[0034] Substrate 1 (1 mmol) was dissolved in toluene (2 mL), ZnCl was added 2 (0.2mmol, 27mg), the reaction mixture was heated to 140°C and stirred for 4 hours. After the reaction was completed, the target product a was separated by flash column chromatography with a yield of 40%. Its reaction equation is:
[0035]
[0036] The spectral data of product a is: 1 H NMR (600MHz, CDCl3 )δ7.46(d, J=7.4Hz, 2H), 7.42(d, J=7.1Hz, 2H), 7.39(t, J=8.4Hz, 5H), 7.33(m, 2H), 7.25(m, 5H), 7.08(d, J=2.2Hz, 1H), 6.97(dd, J=8.5, 2.2Hz, 1H), 6.32(d, J=2.2Hz, 1H), 6.29(d, J=2.2Hz, 1H), 5.93(s,1H), 5.12(s,2H), 5.04(s,2H), 5.02(s,2H), 2.09(s,3H); 13 C NMR (150MHz, CDCl 3 )δ161.7,158.6,157.3,156.7,155.6,143.9,137.1,136.8,136.7,128.8,128.7,128.6,128.3,128.1,127.8,127.7,127.6,127.1,124.1,119.7,115.8,112.2,100.4,97.3,94.7 ,94.2,70.8,70.6,70.30,9.26; HRMS(ESI):m / z:Calcd.for C 36 h 30 o 5 [M+H] + 543.2166, Found 543.2173.
Embodiment 3
[0038] Substrate 1 (1 mmol) was dissolved in dichloromethane (2 mL), silica gel (1 g) was added, dichloromethane was evaporated to dryness by distillation under reduced pressure, the reaction mixture was heated to 140° C., and the reaction was stirred for 4 hours. After the reaction was completed, The target product a was separated by flash column chromatography with a yield of 75%. Its reaction equation is:
[0039]
[0040] The spectral data of product a is: 1 H NMR (600MHz, CDCl 3 )δ7.46(d, J=7.4Hz, 2H), 7.42(d, J=7.1Hz, 2H), 7.39(t, J=8.4Hz, 5H), 7.33(m, 2H), 7.25(m, 5H), 7.08(d, J=2.2Hz, 1H), 6.97(dd, J=8.5, 2.2Hz, 1H), 6.32(d, J=2.2Hz, 1H), 6.29(d, J=2.2Hz, 1H), 5.93(s,1H), 5.12(s,2H), 5.04(s,2H), 5.02(s,2H), 2.09(s,3H); 13 C NMR (150MHz, CDCl 3 )δ161.7,158.6,157.3,156.7,155.6,143.9,137.1,136.8,136.7,128.8,128.7,128.6,128.3,128.1,127.8,127.7,127.6,127.1,124.1,119.7,115.8,112.2,100.4,97.3,94.7 ,94.2,70.8,70.6,70.30,9.26; HRMS(ESI):m / z:Calcd.for C 36 h 30 o 5 [...
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