CTV (Cyclotriveratrylene)-I3 derivative and preparation method thereof
A technology of CTV-I3 and derivatives, applied in the field of preparation of CTV-I3 derivatives, can solve the problems of high yield cost, long steps, unfavorable product purification and the like, and achieve the effect of high yield
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Embodiment 1
[0040] Example 1, Propoxy CTV-I 3 Preparation
[0041] (1) Preparation of propyl 3-propoxy-4-iodobenzoate
[0042] The reaction equation is as follows:
[0043]
[0044] Add 8g (30.3mmol) of 3-hydroxy-4-iodobenzoic acid to a 500mL round bottom flask, Cs 2 CO 3 40g (2equiv.), add 9g of n-propyl bromide (2.4equiv.) and 200mL of acetone. The reaction system was reacted at 60°C for 12 hours; after the reaction, solid impurities were removed by filtration, and acetone was removed by rotary evaporation. The reaction product was extracted with water and dichloromethane for liquid separation, dried and filtered, and the dichloromethane was removed by rotary evaporation to obtain 6.85 g of propyl 3-propoxy-4-iodobenzoate, 65%.
[0045] 1 H NMR(400MHz, CDCl 3 ): δ7.84-7.82(d,1H),7.42-7.41(d,1H),7.36-7.34(m,1H), 4.29-4.25(t,2H),4.06-4.03(t,2H),1.91 -1.74(m,4H), 1.12-1.08(t,3H), 1.04-1.00(t,3H). 13 C NMR(100MHz, CDCl 3 ): δ166.2, 157.7, 139.3, 131.9, 123.0, 112.2, 93.1, 70.9, 66.8, 22.4, 22.1,...
Embodiment 2
[0056] Example 2. Butoxy CTV-I 3 Preparation
[0057] (1) Preparation of butyl 3-butoxy-4-iodobenzoate
[0058] The reaction equation is as follows:
[0059]
[0060] Add 8g (30.3mmol) of 3-hydroxy-4-iodobenzoic acid to a 500mL round bottom flask, Cs 2 CO 3 40g (2equiv.), add n-butyl bromide 10 (2.4equiv.) and 200mL of acetone. The reaction system was reacted at 60°C for 12h. After the reaction, the solid impurities are removed by filtration, and acetone is removed by rotary evaporation. The reaction product was extracted with water and dichloromethane for liquid separation, dried and filtered, and the dichloromethane was removed by rotary evaporation to obtain 6.67 g of butyl 3-butoxy-4-iodobenzoate, 58%.
[0061] 1 H NMR(400MHz, CDCl 3 ): δ7.84-7.82(d,1H),7.41(s,1H),7.354-7.351(d,1H),4.33-4.30(t,2H),4.09-4.06(t,2H),1.86-1.80 (m, 2H), 1.76-1.71 (m, 2H), 1.59-1.43 (m, 4H), 1.02-0.96 (m, 6H). 13 C NMR(100MHz, CDCl 3 ): δ166.2, 157.7, 139.3, 131.9, 123.0, 112.2, 93.1, 69.1, 65.1, 31...
Embodiment 3
[0071] Example 3. The butoxy CTV-I prepared in Example 2 3 Used in Sonogashira reaction to prepare large conjugated aromatic systems
[0072] (1) Butoxy CTV-I 3 Sonogashira reaction with the alkynyl compound represented by formula IV
[0073]
[0074] Under argon conditions, 3mg of phosphorus pentoxide (0.016mmol, 4mol%), PdCl 2 (PPh 3 ) 2 10mg (0.014mmol, 4mol-%), butoxy CTV-I 3 200mg (0.231mmol) and 10mL Et 3 N was added to the Sclenk tube, and after stirring for 0.5 h, the formula IV (1.3 mmol, 1.2 equiv.) was dissolved in 10 mL of THF and added to the reaction system. The reaction system was reacted at 50°C for 24 hours. After the reaction is over, the solvent is removed by rotary evaporation and liquid separation is carried out with dichloromethane and water. The organic phase was dried with anhydrous sodium sulfate, dried and filtered, dichloromethane was removed by rotary evaporation, and then column chromatography was used for separation, using dichloromethane and petrole...
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