1,2-Dichloroethane → N-[2-bromo-4-[3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-butenoyl]phenylmethyl]phthalimide

To a solution of 2.00 g of 1-(3-bromo-4-methylphenyl)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-2-butene-1-one in 15 mL of 1,2-dichloroethane, 0.98 g of N-bromosuccinimide and 0.06 g of α,α′-azobisisobutyronitrile were added, and the resultant reaction mixture was stirred while heating the reaction mixture to reflux for 1 hour. Next, to the reaction mixture, 0.61 g of N-bromosuccinimide and 0.05 g of α,α′-azobisisobutyronitrile were added and the reaction mixture was continued to be stirred at the same temperature further for 2 hours. After the completion of the reaction, the reaction mixture was left to be cooled down to room temperature and was diluted with 50 mL of chloroform. Subsequently, the diluted reaction mixture was washed with water (30 mL×2) and then dehydrated and dried over a saturated brine and anhydrous sodium sulfate in this order, and the solvent was distilled off under reduced pressure. The resultant residue was dissolved in 10 mL of N,N-dimethylformamide, and 0.85 g of phthalimide potassium was added to the resultant solution, followed by stirring the resultant reaction mixture at room temperature for 13 hours. After the completion of the reaction, 30 mL of water was added to the reaction mixture and the resultant reaction mixture was extracted with ethyl acetate (50 mL×1). The organic phase was dehydrated and dried over a saturated brine and anhydrous magnesium sulfate in this order and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1:1) to obtain 1.67 g of the objective substance as a yellow crystal.

1. customthe resultant reaction mixture
2. temperaturewhile heating the reaction mixture
3. temperatureto reflux for 1 hour
4. stirringto be stirred at the same temperature further for 2 hours
5. customAfter the completion of the reaction
6. waitthe reaction mixture was left
7. customSubsequently, the diluted reaction mixture
8. washwas washed with water (30 mL×2)
9. dry with materialdried over a saturated brine and anhydrous sodium sulfate in this order
10. distillationthe solvent was distilled off under reduced pressure
11. dissolutionThe resultant residue was dissolved in 10 mL of N,N-dimethylformamide
12. addition0.85 g of phthalimide potassium was added to the resultant solution
13. stirringby stirring the resultant
14. customreaction mixture at room temperature for 13 hours
15. additionwas added to the reaction mixture
16. customthe resultant reaction mixture
17. extractionwas extracted with ethyl acetate (50 mL×1)
18. dry with materialdried over a saturated brine and anhydrous magnesium sulfate in this order
19. distillationthe solvent was distilled off under reduced pressure
20. customThe resultant residue was purified by silica gel column chromatography
21. washeluting with ethyl acetate-hexane (1:1)
22. customto obtain 1.67 g of the objective substance as a yellow crystal

ORD record

ord-483ac413729e42caad37dce089e5f2d5

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08268754B2