The preparation method of benzoate compound
A technology of ester compounds and compounds, applied in the field of preparation of benzoic acid ester compounds, can solve the problems of high preparation temperature, complicated preparation conditions, low yield, etc.
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[0017] The invention provides a kind of preparation method of the benzoic acid ester compound of structure shown in formula (I), this method comprises: under the condition of exposure, the compound PyboxCu(II) of structure shown in formula (II) Br 2 , compound A1 of structure shown in formula (III), compound A2 and K of structure shown in formula (IV) 4 [Fe(CN) 6 ]·3H 2 O for a contact reaction,
[0018]
[0019] Among them, R 1 Is H or C1-C6 alkyl; R 2 Is H, halogen, C1-C6 alkyl or C1-C6 alkoxy; R 3 Is H, halogen, C1-C6 alkyl or C1-C6 alkoxy; R 4 is H or C1-C6 alkyl.
[0020] The inventors of the present invention speculate that the mechanism of the above-mentioned contact reaction may be as follows figure 1 As shown, compound A1 is in CN - is oxidized to intermediate compound M1 in the presence of; in PyboxCu(II)Br 2 Next, bromine substitution occurs on the α-C of the carbonyl group of compound A2 to generate intermediate compound M2, and compound M1 and compoun...
preparation example 1
[0035] Preparation of 6-bis[4-(1,1-dimethyl)-2-oxazolin-2-yl]pyridine:
[0036] In a 100 mL round bottom flask, add pyridine 2,6-dicarboxylate (2.5 g, 15 mmol) and 15 mL thionyl chloride, reflux at 100° C. for 10 hours, cool the mixture, and remove the solvent to obtain a white solid. The resulting white solid was dissolved in 30 mL of CHCl 3 Add triethylamine (1.3g, 12.45mmol) and 2,2'-dimethylaminoethanol (7g, 7.8mmol), mix well, and stir at 25°C for 20 hours. Slowly add 3 mL of thionyl chloride dropwise, and reflux at 100°C for 2 hours. Then, the organic phase was extracted with ice water, saturated brine and potassium carbonate solution in sequence, and the organic phase was spin-dried. Add 5 ml of saturated sodium hydroxide solution to the organic phase, and stir at 25°C for 3 days. The mixed solution was then extracted with dichloromethane and the organic phase was saved. Finally, the obtained organic phase was dried with magnesium sulfate, and the solvent was remove...
preparation example 2
[0039] The compound PyboxCu(II)Br of structure shown in formula (II) 2 Preparation of:
[0040]
[0041] Under the condition of 25℃ and nitrogen protection, 0.2mmol copper bromide, 0.20mmol 2,6-bis[4-(1,1-dimethyl)-2-oxazolin-2-yl]pyridine, 15ml, methanol and 10ml of dichloromethane solvent were added to a 50mL one-necked flask and magnetically stirred, and after ultrasonic mixing, stirred for 5 hours. The resulting mixture was then removed from the solvent with a rotary evaporator, washed with ether, then added with 5ml of dichloromethane, ultrasonically dissolved, filtered to get the filtrate, and concentrated to obtain 95 mg of the dark green solid compound PyboxCu(II)Br 2 , the yield was 96%.
[0042] Compound PyboxCu(II)Br 2 The characterization data is: Anal.Calcd.for (elemental analysis) C 15 h 19 Br 2 CuN 3 o 2 :C36.27,H3.86,N8.46Found:C36.18,H3.65,N8.50.IR(KBrcm -1 ):3025(m), 2968(w), 2929(w), 1643(m), 1624(s), 1573(s), 1497(m), 1452(w), 1401(s), 1381(m )...
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