* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20.0℃; for 2.0h;Cooling with ice;
General procedure: To a solution of cinnamic acid (10 mmol) in dichloromethane(30 mL) in an ice bath was added a mixture of oxalyl chloride (1.5 mL, 17.5 mmol) and dimethylformamide (2drops). After the mixture was stirred for 2 h at room temperature, the solvent was removed under reduced pressure to givecinnamoyl chloride which was mixed with 3,4,5-trimethoxyphenol (1.8 g, 10 mmol) and then dissolved in boron trifluoride etherate (10 mL) and heated to reflux for 10 min. After cooling, the mixture was poured into ice water and then the precipitate was filtered and washed with water until free from acid. The resulting precipitate was washed with hexane and then with ether to obtain the corresponding chalcones 1a-m (89-97%) as orange-yellow powders. A mixture of chalcones 1a-m (10 mmol) and iodine (1.0 eq) in DMSO (25 mL) was heated toreflux for 3 h. After cooling, the mixture was poured into icewater. The precipitate was filtered and washed with saturated sodium thiosulfate solution. The residue was chromatographed on a silica gel column with hexane/EtOAc (2 : 1) as the eluent to give pure 2a-m as pale yellow solids. The preparation of 3a-j (Chart 2) were essentially according to our published procedure. 20) All the physicochemical and spectroscopic characteristics of products 2a-j and 3a-j are in agreement with those reported.20)
With thionyl chloride; at 100.0℃; for 2.0h;
3-(3-Bromo-4-fluoro-phenyl)-acrylic acid (3.3 g, 13.3 mmol) prepared in Step 1 was added to thionyl chloride (10.0 mL). The reaction mixture was stirred at 100 C. for 2 hours, concentrated under reduced pressure. The resulting residue was concentrated under reduced pressure three times, along with using toluene, to give 3.5 g of the titled compound as an unpurified dark brown liquid. (0156) 1H NMR (400 MHz, CDCl3) 7.93 (d, 1H), 7.66-7.62 (m, 2H), 7.27 (t, 1H), 6.54 (d, 1H)
3-Bromo-4-fluoro-benzaldehyde (5.0 g, 24.6 mmol), malonic acid (5.6 g, 53.7 mmol), and piperidine (0.5 mL, 4.9 mmol) were added to pyridine (11.4 mL). The reaction mixture was stirred at 100 C. for 3 hours and then concentrated under reduced pressure. Distilled water was added to the reaction mixture, which was then filtered. The resulting solid was recrystallized from ethanol to give 3.3 g of the titled compound as a white solid. (0154) 1H NMR (400 MHz, CD3OD) 7.93 (d, 1H), 7.64-7.60 (m, 2H), 7.27 (t, 1H), 6.49 (d, 1H)
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
Life Science
For Research Only
100K+ Compounds
Competitive Price
1-2 Day Shipping
