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The preparation method is as follows:Ethylene glycol acetal (458 mg, 2 mmol) of 3-bromobenzaldehyde,Dissolved in 5 mL of dry tetrahydrofuran,N-Butyllithium (0.8 mL, 2 mmol) was slowly added dropwise at -70 C,One hour later, N-methyl-N-methoxy 4-fluorobenzamide was added slowly at -70 C(311 mg, 1.7 mmol),The reaction was continued at -70 C for 2 hours,The reaction was quenched by adding 5 mL saturated brine and the organic phase was extracted with ethyl acetate (10 mL * 3)The combined organic phases are dried over anhydrous sodium sulphate. Spin the solvent,Column chromatography (petroleum ether: ethyl acetate = 20: 1 as eluant),The reaction product 347mg.The reaction product was dissolved in 5 mL of dry methanol,1mL6N hydrochloric acid was added at room temperature, the reaction for 1 hour,The reaction was quenched by addition of saturated sodium bicarbonate solution,The organic phase was extracted with ethyl acetate (10 mL * 3), the organic phases were combined,Drying over anhydrous sodium sulfate. Spin the solvent,Column chromatography (petroleum ether: ethyl acetate = 20: 1 as eluant),The reaction product of 3- (4-fluorobenzoyl) acylbenzaldehyde 264mg, 68% yield in two steps.
1.37 g
To a solution of n-BuLi (9.31 mL, 14.89 mmol, 1.6 M) in dry THF(20 mL) at -78 C under nitrogen atmosphere, Compound 2 (1.71 g,7.45 mmol) in THF (12 mL) solution was added dropwise. Then, the solution was stirred at -78 C under nitrogen atmosphere for 1.5 h. Compound 1 (1.50 g, 8.19 mmol) in THF (12 mL) solution at -78 C was added. After the reaction was stirred to complete, the mixture was filtered, and the solvent was removed under reduced pressure. The residue was washed with water, extracted with DCM and purified bysilica gel column chromatography using petroleum ether/ethyl acetate (20:3) to give colourless oil Compound 3 (1.37 g, 5.05 mmol). The Compound 3 (1.37 g, 5.05 mmol) was dissolved in acetonitrile (10 mL),then the solution was added 2M HCl (8 mL, 15.14 mmol) and stirred at 25 C overnight. After the reaction was stirred to complete, the mixture was filtered, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography using petroleumether/ethyl acetate (10:1) to give colourless oil Compound 5b (869.52 mg, 3.81 mmol, 51.2% yield for 2 steps).
To a solution of 4-fluorophenol (500mg, 4.46mol) in dry DCM (10ml), (3-formylphenyl)boronic acid(1.00g, 6.69mol), Cu(OAc)2 (811mg, 4.46mol) and Et3N (135.6mg, 1.34mol) were added under O2 atmosphere and the mixture was stirred at 25C for 48h. The mixture was diluted with brine and extracted with EtOAc. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography using petroleum ether/ethyl acetate (10:1) to produce 0.22g of 0.22g with a yield of 22%. To a solution of 4-fluorophenol (500mg, 4.46mol) in dry DCM (10ml), (3-formylphenyl)boronic acid(1.00g, 6.69mol), Cu(OAc)2 (811mg, 4.46mol) and Et3N (135.6mg, 1.34mol) were added under O2 atmosphere and the mixture was stirred at 25C for 48h. The mixture was diluted with brine and extracted with EtOAc. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography using petroleum ether/ethyl acetate (10:1) to produce 0.22g of 0.22g with a yield of 22%.
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