Preparation method of indanone compound
A compound and a technology for indanone, which is applied in the field of preparation of indanone compounds, can solve problems such as difficult separation of products, and achieve the effects of easy availability of raw materials, high product yield and simple method
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[0021] The present invention at first provides a kind of preparation method of indanone compound, and this method comprises:
[0022] Under the action of nickel catalyst, ligand, biboronic acid pinacol ester, alkali and water, react o-bromophenylcyclobutanone with the structure of formula 1 in a solvent at 70°C to 90°C for 12 to 24 hours, and the reaction ends After separation and purification of the product, the indanone compound of the formula I structure is obtained;
[0023]
[0024] In formula 1 and formula I, R 1 is a hydrogen atom, a fluorine atom, a methyl group, a trifluoromethyl group or an alkoxy group, preferably a methyl group or an alkoxy group.
[0025] According to the present invention, described nickel catalyst is preferably NiBr 2 、NiBr 2 ·CH 3 OCH 2 CH 2 OCH 3 , Ni(OTf) 2 or Ni(COD) 2 , more preferably NiBr 2 ; The ligand is preferably neocopper reagent, 3,4,7,8-tetramethyl-1,10-phenanthroline, 5,6-dimethyl-1,10-phenanthroline, 4- Methyl-1,10-...
Embodiment 1
[0036] 1. Reaction formula:
[0037]
[0038] 2. The amount and properties of the reaction raw materials are shown in Table 1:
[0039] Table 1
[0040]
[0041] Three, the preparation is as follows:
[0042] Add a magnetic stir bar to the sealed tube, 3-(2-bromo-5-methylphenyl)cyclobutan-1-one (71.7mg, 0.3mmol), NiBr 2 (6.6mg, 0.03mmol), Neocuproine (13.7mg, 0.066mmol), B 2 Pin 2 (152.4mg, 0.6mmol), Na 2 CO 3(63.6mg, 0.6mmol), the system was protected by argon. Dissolve 3-(2-bromo-5-methylphenyl)cyclobutan-1-one (0.3mmol) and water (0.6mmol) in 3mL DMF, quickly add the sealed tube with a 5mL syringe, and then seal the Tube sealed. Place the sealed tube in an oil bath on a magnetic stirrer with a heating function, stir and react at a constant temperature of 80° C. for 13 hours, and monitor the reaction by thin-layer chromatography. After cooling to room temperature, add 3mL of 2mol / L dilute hydrochloric acid, stir for 3 minutes to neutralize the remaining alkali...
Embodiment 2
[0046] 1. Reaction formula:
[0047]
[0048] 2. R in the reaction formula 1 , R 2 When being different substituents, prepare indanone compounds, the preparation method is the same as Example 1, and the results are as shown in table 2:
[0049] Table 2
[0050]
[0051] The results show that this method has a wide range of applications, and a wide range of substrates can be used to synthesize corresponding compounds.
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